ORD record viewer · decoder definitions: ord-schema 0.8.3
Table numbers are rounded to 7 significant digits; decoded details retain full precision.
Gesmundo et al. 2018 Nature: nanomole-scale synthesis and affinity ranking
Dataset description
Reactions from N. J. Gesmundo, B. Sauvagnat, P. J. Curran, M. P. Richards, C. L. Andrews, P. J. Dandliker, T. Cernak, 'Nanoscale synthesis and affinity ranking', Nature 2018, 557, 228-232 (doi:10.1038/s41586-018-0056-8). One dataset combining several screens and libraries: SI 3.2 Suzuki screen (ED Fig. 6): 672 reactions; SI 3.3 Suzuki screen on 7 (ED Fig. 6): 162 reactions; SI 3.4 C-N screen 1 (ED Fig. 6): 384 reactions; SI 3.5 C-N screen 2 (ED Fig. 6): 360 reactions; SI 3.6 diverse nucleophile screen (ED Fig. 6): 1536 reactions; SI 5.2 pERK2 amide nano library (Fig. 2a): 38 reactions; SI 6.2 MK2 Suzuki nano library (Fig. 2b): 144 reactions; SI 7.2 CHK1 mixed nano library (Fig. 2c): 200 reactions; SI 8.2 384-member library, variable conditions (Fig. 3): 1536 reactions; SI 8.3 384-member library, single condition (Fig. 3): 384 reactions; SI 5.1 bench-scale pERK2 amides (isolated): 19 reactions; SI 6.1 bench-scale MK2 Suzuki couplings (isolated): 18 reactions; SI 7.1 bench-scale CHK1 couplings (isolated): 20 reactions; SI 8.6 bench-scale CHK1 library scale-ups (isolated): 59 reactions; Nanomole-scale reactions (1-1.2 uL, 1,536-well plates, N2 glove box, ambient temperature) report LC-UV yields (internal standard or standard curve; not isolated) and/or relative conversions from the Source Data spreadsheets; bench-scale reactions report isolated yields from the SI. Duplicate sheets ('Compiled Yield Data', 'prelim-screening-csv', MOESM4-9 copies) were not used. ASMS affinity data are out of scope.
Decoded from the bound file. This is a read-only preview, not schema validation or scientific verification. Missing values remain unreported; AREA is not relabeled as YIELD.
| Location | Record | Inputs and roles | Temperature | Reported measurements | Source |
|---|---|---|---|---|---|
| reactions[0] | Record 1 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1ccccc1 CATALYST: XPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · IDENTITY: — [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 32.3% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 359696.5 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[0]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_001"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "XPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A1",
"row": "A",
"col": "1"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: XPhos Pd G3 / P2-Et / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 38.78499984741211
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "product detected by UPLC-MS ([M+H]+) with a UV peak at the expected retention time"
},
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 32.29999923706055
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 359696.46875
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[1] | Record 2 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1ccccc1 CATALYST: tBuXPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[1]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_002"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)C(C)(C)C)c(C(C)C)c1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "tBuXPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A2",
"row": "A",
"col": "2"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: tBuXPhos Pd G3 / P2-Et / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[2] | Record 3 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1ccccc1 CATALYST: tBu3P Pd G2 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[2]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_003"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(C(C)(C)C)C(C)(C)C.Cl[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "tBu3P Pd G2 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A3",
"row": "A",
"col": "3"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: tBu3P Pd G2 / P2-Et / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[3] | Record 4 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1ccccc1 CATALYST: DTBPF Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[3]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_004"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(C(C)(C)C)c1ccc[cH-]1.CC(C)(C)P(C(C)(C)C)c1ccc[cH-]1.[Fe+2].CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "DTBPF Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A4",
"row": "A",
"col": "4"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: DTBPF Pd G3 / P2-Et / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[4] | Record 5 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: tert-butylimino-tri(pyrrolidino)phosphorane (BTTP) REACTANT: OB(O)c1ccccc1 CATALYST: XPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[4]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_005"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1"
},
{
"type": "NAME",
"value": "tert-butylimino-tri(pyrrolidino)phosphorane (BTTP)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "XPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A5",
"row": "A",
"col": "5"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: XPhos Pd G3 / BTTP / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[5] | Record 6 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: tert-butylimino-tri(pyrrolidino)phosphorane (BTTP) REACTANT: OB(O)c1ccccc1 CATALYST: tBuXPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[5]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_006"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1"
},
{
"type": "NAME",
"value": "tert-butylimino-tri(pyrrolidino)phosphorane (BTTP)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)C(C)(C)C)c(C(C)C)c1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "tBuXPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A6",
"row": "A",
"col": "6"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: tBuXPhos Pd G3 / BTTP / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[6] | Record 7 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: tert-butylimino-tri(pyrrolidino)phosphorane (BTTP) REACTANT: OB(O)c1ccccc1 CATALYST: tBu3P Pd G2 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[6]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_007"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1"
},
{
"type": "NAME",
"value": "tert-butylimino-tri(pyrrolidino)phosphorane (BTTP)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(C(C)(C)C)C(C)(C)C.Cl[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "tBu3P Pd G2 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A7",
"row": "A",
"col": "7"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: tBu3P Pd G2 / BTTP / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[7] | Record 8 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: tert-butylimino-tri(pyrrolidino)phosphorane (BTTP) REACTANT: OB(O)c1ccccc1 CATALYST: DTBPF Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[7]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_008"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1"
},
{
"type": "NAME",
"value": "tert-butylimino-tri(pyrrolidino)phosphorane (BTTP)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(C(C)(C)C)c1ccc[cH-]1.CC(C)(C)P(C(C)(C)C)c1ccc[cH-]1.[Fe+2].CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "DTBPF Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A8",
"row": "A",
"col": "8"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: DTBPF Pd G3 / BTTP / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[8] | Record 9 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: 2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG) REACTANT: OB(O)c1ccccc1 CATALYST: XPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[8]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_009"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C(=NC(C)(C)C)N(C)C"
},
{
"type": "NAME",
"value": "2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "XPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A9",
"row": "A",
"col": "9"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: XPhos Pd G3 / BTMG / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[9] | Record 10 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: 2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG) REACTANT: OB(O)c1ccccc1 CATALYST: tBuXPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[9]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_010"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C(=NC(C)(C)C)N(C)C"
},
{
"type": "NAME",
"value": "2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)C(C)(C)C)c(C(C)C)c1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "tBuXPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A10",
"row": "A",
"col": "10"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: tBuXPhos Pd G3 / BTMG / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[10] | Record 11 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: 2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG) REACTANT: OB(O)c1ccccc1 CATALYST: tBu3P Pd G2 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[10]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_011"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C(=NC(C)(C)C)N(C)C"
},
{
"type": "NAME",
"value": "2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(C(C)(C)C)C(C)(C)C.Cl[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "tBu3P Pd G2 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A11",
"row": "A",
"col": "11"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: tBu3P Pd G2 / BTMG / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[11] | Record 12 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: 2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG) REACTANT: OB(O)c1ccccc1 CATALYST: DTBPF Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[11]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_012"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C(=NC(C)(C)C)N(C)C"
},
{
"type": "NAME",
"value": "2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(C(C)(C)C)c1ccc[cH-]1.CC(C)(C)P(C(C)(C)C)c1ccc[cH-]1.[Fe+2].CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "DTBPF Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A12",
"row": "A",
"col": "12"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: DTBPF Pd G3 / BTMG / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[12] | Record 13 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) REACTANT: OB(O)c1ccccc1 CATALYST: XPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[12]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_013"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCN2CCCN=C12"
},
{
"type": "NAME",
"value": "7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "XPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A13",
"row": "A",
"col": "13"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: XPhos Pd G3 / MTBD / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[13] | Record 14 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) REACTANT: OB(O)c1ccccc1 CATALYST: tBuXPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[13]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_014"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCN2CCCN=C12"
},
{
"type": "NAME",
"value": "7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)C(C)(C)C)c(C(C)C)c1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "tBuXPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A14",
"row": "A",
"col": "14"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: tBuXPhos Pd G3 / MTBD / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[14] | Record 15 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) REACTANT: OB(O)c1ccccc1 CATALYST: tBu3P Pd G2 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[14]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_015"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCN2CCCN=C12"
},
{
"type": "NAME",
"value": "7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(C(C)(C)C)C(C)(C)C.Cl[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "tBu3P Pd G2 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A15",
"row": "A",
"col": "15"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: tBu3P Pd G2 / MTBD / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[15] | Record 16 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) REACTANT: OB(O)c1ccccc1 CATALYST: DTBPF Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[15]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_016"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCN2CCCN=C12"
},
{
"type": "NAME",
"value": "7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(C(C)(C)C)c1ccc[cH-]1.CC(C)(C)P(C(C)(C)C)c1ccc[cH-]1.[Fe+2].CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "DTBPF Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A16",
"row": "A",
"col": "16"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: DTBPF Pd G3 / MTBD / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[16] | Record 17 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1ccccc1 CATALYST: XPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone SOLVENT: tert-amyl alcohol | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · IDENTITY: — [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 8.4% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 99630.02 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[16]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_017"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "XPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 0.8999999761581421,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "tert-amyl alcohol"
}
],
"amount": {
"volume": {
"value": 0.10000000149011612,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A17",
"row": "A",
"col": "17"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: XPhos Pd G3 / P2-Et / 10%tAmOH/NMP; base dispensed in 40% t-AmOH/NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 14.533395767211914
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "product detected by UPLC-MS ([M+H]+) with a UV peak at the expected retention time"
},
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 8.399999618530273
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 99630.015625
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[17] | Record 18 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1ccccc1 CATALYST: tBuXPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone SOLVENT: tert-amyl alcohol | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[17]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_018"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)C(C)(C)C)c(C(C)C)c1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "tBuXPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 0.8999999761581421,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "tert-amyl alcohol"
}
],
"amount": {
"volume": {
"value": 0.10000000149011612,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A18",
"row": "A",
"col": "18"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: tBuXPhos Pd G3 / P2-Et / 10%tAmOH/NMP; base dispensed in 40% t-AmOH/NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[18] | Record 19 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1ccccc1 CATALYST: tBu3P Pd G2 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone SOLVENT: tert-amyl alcohol | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[18]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_019"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(C(C)(C)C)C(C)(C)C.Cl[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "tBu3P Pd G2 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 0.8999999761581421,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "tert-amyl alcohol"
}
],
"amount": {
"volume": {
"value": 0.10000000149011612,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A19",
"row": "A",
"col": "19"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: tBu3P Pd G2 / P2-Et / 10%tAmOH/NMP; base dispensed in 40% t-AmOH/NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[19] | Record 20 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1ccccc1 CATALYST: DTBPF Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone SOLVENT: tert-amyl alcohol | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · IDENTITY: — [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 1.9% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 28507.56 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[19]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_020"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(C(C)(C)C)c1ccc[cH-]1.CC(C)(C)P(C(C)(C)C)c1ccc[cH-]1.[Fe+2].CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "DTBPF Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 0.8999999761581421,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "tert-amyl alcohol"
}
],
"amount": {
"volume": {
"value": 0.10000000149011612,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A20",
"row": "A",
"col": "20"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: DTBPF Pd G3 / P2-Et / 10%tAmOH/NMP; base dispensed in 40% t-AmOH/NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 2.2437314987182617
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "product detected by UPLC-MS ([M+H]+) with a UV peak at the expected retention time"
},
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 1.899999976158142
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 28507.55859375
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[20] | Record 21 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: tert-butylimino-tri(pyrrolidino)phosphorane (BTTP) REACTANT: OB(O)c1ccccc1 CATALYST: XPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone SOLVENT: tert-amyl alcohol | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[20]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_021"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1"
},
{
"type": "NAME",
"value": "tert-butylimino-tri(pyrrolidino)phosphorane (BTTP)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "XPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 0.8999999761581421,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "tert-amyl alcohol"
}
],
"amount": {
"volume": {
"value": 0.10000000149011612,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A21",
"row": "A",
"col": "21"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: XPhos Pd G3 / BTTP / 10%tAmOH/NMP; base dispensed in 40% t-AmOH/NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[21] | Record 22 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: tert-butylimino-tri(pyrrolidino)phosphorane (BTTP) REACTANT: OB(O)c1ccccc1 CATALYST: tBuXPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone SOLVENT: tert-amyl alcohol | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[21]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_022"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1"
},
{
"type": "NAME",
"value": "tert-butylimino-tri(pyrrolidino)phosphorane (BTTP)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)C(C)(C)C)c(C(C)C)c1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "tBuXPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 0.8999999761581421,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "tert-amyl alcohol"
}
],
"amount": {
"volume": {
"value": 0.10000000149011612,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A22",
"row": "A",
"col": "22"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: tBuXPhos Pd G3 / BTTP / 10%tAmOH/NMP; base dispensed in 40% t-AmOH/NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[22] | Record 23 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: tert-butylimino-tri(pyrrolidino)phosphorane (BTTP) REACTANT: OB(O)c1ccccc1 CATALYST: tBu3P Pd G2 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone SOLVENT: tert-amyl alcohol | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[22]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_023"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1"
},
{
"type": "NAME",
"value": "tert-butylimino-tri(pyrrolidino)phosphorane (BTTP)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(C(C)(C)C)C(C)(C)C.Cl[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "tBu3P Pd G2 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 0.8999999761581421,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "tert-amyl alcohol"
}
],
"amount": {
"volume": {
"value": 0.10000000149011612,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A23",
"row": "A",
"col": "23"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: tBu3P Pd G2 / BTTP / 10%tAmOH/NMP; base dispensed in 40% t-AmOH/NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[23] | Record 24 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: tert-butylimino-tri(pyrrolidino)phosphorane (BTTP) REACTANT: OB(O)c1ccccc1 CATALYST: DTBPF Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone SOLVENT: tert-amyl alcohol | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[23]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_024"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1"
},
{
"type": "NAME",
"value": "tert-butylimino-tri(pyrrolidino)phosphorane (BTTP)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(C(C)(C)C)c1ccc[cH-]1.CC(C)(C)P(C(C)(C)C)c1ccc[cH-]1.[Fe+2].CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "DTBPF Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 0.8999999761581421,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "tert-amyl alcohol"
}
],
"amount": {
"volume": {
"value": 0.10000000149011612,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "A24",
"row": "A",
"col": "24"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: DTBPF Pd G3 / BTTP / 10%tAmOH/NMP; base dispensed in 40% t-AmOH/NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[24] | Record 25 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1ccccc1 CATALYST: SPhos Pd G2 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · IDENTITY: — [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 27.5% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 307856.2 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[24]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_025"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cl[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "SPhos Pd G2 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B1",
"row": "B",
"col": "1"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: SPhos Pd G2 / P2-Et / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 24.987695693969727
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "product detected by UPLC-MS ([M+H]+) with a UV peak at the expected retention time"
},
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 27.5
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 307856.1875
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[25] | Record 26 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1ccccc1 CATALYST: RuPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[25]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_026"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "RuPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B2",
"row": "B",
"col": "2"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: RuPhos Pd G3 / P2-Et / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[26] | Record 27 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1ccccc1 CATALYST: BrettPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[26]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_027"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(OC)c(P(C2CCCCC2)C2CCCCC2)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "BrettPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B3",
"row": "B",
"col": "3"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: BrettPhos Pd G3 / P2-Et / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[27] | Record 28 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1ccccc1 CATALYST: APhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[27]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_028"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)c1ccc(P(C(C)(C)C)C(C)(C)C)cc1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "APhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B4",
"row": "B",
"col": "4"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: APhos Pd G3 / P2-Et / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[28] | Record 29 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: tert-butylimino-tri(pyrrolidino)phosphorane (BTTP) REACTANT: OB(O)c1ccccc1 CATALYST: SPhos Pd G2 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[28]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_029"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1"
},
{
"type": "NAME",
"value": "tert-butylimino-tri(pyrrolidino)phosphorane (BTTP)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cl[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "SPhos Pd G2 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B5",
"row": "B",
"col": "5"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: SPhos Pd G2 / BTTP / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[29] | Record 30 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: tert-butylimino-tri(pyrrolidino)phosphorane (BTTP) REACTANT: OB(O)c1ccccc1 CATALYST: RuPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[29]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_030"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1"
},
{
"type": "NAME",
"value": "tert-butylimino-tri(pyrrolidino)phosphorane (BTTP)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "RuPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B6",
"row": "B",
"col": "6"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: RuPhos Pd G3 / BTTP / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[30] | Record 31 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: tert-butylimino-tri(pyrrolidino)phosphorane (BTTP) REACTANT: OB(O)c1ccccc1 CATALYST: BrettPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[30]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_031"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1"
},
{
"type": "NAME",
"value": "tert-butylimino-tri(pyrrolidino)phosphorane (BTTP)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(OC)c(P(C2CCCCC2)C2CCCCC2)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "BrettPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B7",
"row": "B",
"col": "7"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: BrettPhos Pd G3 / BTTP / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[31] | Record 32 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: tert-butylimino-tri(pyrrolidino)phosphorane (BTTP) REACTANT: OB(O)c1ccccc1 CATALYST: APhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[31]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_032"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1"
},
{
"type": "NAME",
"value": "tert-butylimino-tri(pyrrolidino)phosphorane (BTTP)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)c1ccc(P(C(C)(C)C)C(C)(C)C)cc1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "APhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B8",
"row": "B",
"col": "8"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: APhos Pd G3 / BTTP / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[32] | Record 33 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: 2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG) REACTANT: OB(O)c1ccccc1 CATALYST: SPhos Pd G2 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[32]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_033"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C(=NC(C)(C)C)N(C)C"
},
{
"type": "NAME",
"value": "2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cl[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "SPhos Pd G2 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B9",
"row": "B",
"col": "9"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: SPhos Pd G2 / BTMG / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[33] | Record 34 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: 2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG) REACTANT: OB(O)c1ccccc1 CATALYST: RuPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[33]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_034"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C(=NC(C)(C)C)N(C)C"
},
{
"type": "NAME",
"value": "2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "RuPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B10",
"row": "B",
"col": "10"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: RuPhos Pd G3 / BTMG / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[34] | Record 35 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: 2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG) REACTANT: OB(O)c1ccccc1 CATALYST: BrettPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[34]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_035"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C(=NC(C)(C)C)N(C)C"
},
{
"type": "NAME",
"value": "2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(OC)c(P(C2CCCCC2)C2CCCCC2)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "BrettPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B11",
"row": "B",
"col": "11"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: BrettPhos Pd G3 / BTMG / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[35] | Record 36 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: 2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG) REACTANT: OB(O)c1ccccc1 CATALYST: APhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[35]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_036"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)C(=NC(C)(C)C)N(C)C"
},
{
"type": "NAME",
"value": "2-tert-butyl-1,1,3,3-tetramethylguanidine (BTMG)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)c1ccc(P(C(C)(C)C)C(C)(C)C)cc1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "APhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B12",
"row": "B",
"col": "12"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: APhos Pd G3 / BTMG / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[36] | Record 37 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) REACTANT: OB(O)c1ccccc1 CATALYST: SPhos Pd G2 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[36]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_037"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCN2CCCN=C12"
},
{
"type": "NAME",
"value": "7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cl[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "SPhos Pd G2 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B13",
"row": "B",
"col": "13"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: SPhos Pd G2 / MTBD / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[37] | Record 38 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) REACTANT: OB(O)c1ccccc1 CATALYST: RuPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[37]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_038"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCN2CCCN=C12"
},
{
"type": "NAME",
"value": "7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "RuPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B14",
"row": "B",
"col": "14"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: RuPhos Pd G3 / MTBD / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[38] | Record 39 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) REACTANT: OB(O)c1ccccc1 CATALYST: BrettPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[38]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_039"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCN2CCCN=C12"
},
{
"type": "NAME",
"value": "7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(OC)c(P(C2CCCCC2)C2CCCCC2)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "BrettPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B15",
"row": "B",
"col": "15"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: BrettPhos Pd G3 / MTBD / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[39] | Record 40 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) REACTANT: OB(O)c1ccccc1 CATALYST: APhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[39]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_040"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCN2CCCN=C12"
},
{
"type": "NAME",
"value": "7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)c1ccc(P(C(C)(C)C)C(C)(C)C)cc1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "APhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B16",
"row": "B",
"col": "16"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: APhos Pd G3 / MTBD / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[40] | Record 41 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1ccccc1 CATALYST: SPhos Pd G2 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone SOLVENT: tert-amyl alcohol | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · IDENTITY: — [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 2.5% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 34901.32 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[40]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_041"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cl[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "SPhos Pd G2 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 0.8999999761581421,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "tert-amyl alcohol"
}
],
"amount": {
"volume": {
"value": 0.10000000149011612,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B17",
"row": "B",
"col": "17"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: SPhos Pd G2 / P2-Et / 10%tAmOH/NMP; base dispensed in 40% t-AmOH/NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 2.6501688957214355
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "product detected by UPLC-MS ([M+H]+) with a UV peak at the expected retention time"
},
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 2.5
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 34901.3203125
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[41] | Record 42 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1ccccc1 CATALYST: RuPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone SOLVENT: tert-amyl alcohol | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[41]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_042"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "RuPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 0.8999999761581421,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "tert-amyl alcohol"
}
],
"amount": {
"volume": {
"value": 0.10000000149011612,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B18",
"row": "B",
"col": "18"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: RuPhos Pd G3 / P2-Et / 10%tAmOH/NMP; base dispensed in 40% t-AmOH/NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[42] | Record 43 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1ccccc1 CATALYST: BrettPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone SOLVENT: tert-amyl alcohol | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[42]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_043"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(OC)c(P(C2CCCCC2)C2CCCCC2)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "BrettPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 0.8999999761581421,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "tert-amyl alcohol"
}
],
"amount": {
"volume": {
"value": 0.10000000149011612,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B19",
"row": "B",
"col": "19"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: BrettPhos Pd G3 / P2-Et / 10%tAmOH/NMP; base dispensed in 40% t-AmOH/NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[43] | Record 44 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1ccccc1 CATALYST: APhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone SOLVENT: tert-amyl alcohol | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[43]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_044"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)c1ccc(P(C(C)(C)C)C(C)(C)C)cc1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "APhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 0.8999999761581421,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "tert-amyl alcohol"
}
],
"amount": {
"volume": {
"value": 0.10000000149011612,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B20",
"row": "B",
"col": "20"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: APhos Pd G3 / P2-Et / 10%tAmOH/NMP; base dispensed in 40% t-AmOH/NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[44] | Record 45 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: tert-butylimino-tri(pyrrolidino)phosphorane (BTTP) REACTANT: OB(O)c1ccccc1 CATALYST: SPhos Pd G2 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone SOLVENT: tert-amyl alcohol | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[44]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_045"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1"
},
{
"type": "NAME",
"value": "tert-butylimino-tri(pyrrolidino)phosphorane (BTTP)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.Cl[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "SPhos Pd G2 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 0.8999999761581421,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "tert-amyl alcohol"
}
],
"amount": {
"volume": {
"value": 0.10000000149011612,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B21",
"row": "B",
"col": "21"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: SPhos Pd G2 / BTTP / 10%tAmOH/NMP; base dispensed in 40% t-AmOH/NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[45] | Record 46 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: tert-butylimino-tri(pyrrolidino)phosphorane (BTTP) REACTANT: OB(O)c1ccccc1 CATALYST: RuPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone SOLVENT: tert-amyl alcohol | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[45]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_046"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1"
},
{
"type": "NAME",
"value": "tert-butylimino-tri(pyrrolidino)phosphorane (BTTP)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)Oc1cccc(OC(C)C)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "RuPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 0.8999999761581421,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "tert-amyl alcohol"
}
],
"amount": {
"volume": {
"value": 0.10000000149011612,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B22",
"row": "B",
"col": "22"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: RuPhos Pd G3 / BTTP / 10%tAmOH/NMP; base dispensed in 40% t-AmOH/NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[46] | Record 47 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: tert-butylimino-tri(pyrrolidino)phosphorane (BTTP) REACTANT: OB(O)c1ccccc1 CATALYST: BrettPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone SOLVENT: tert-amyl alcohol | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[46]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_047"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1"
},
{
"type": "NAME",
"value": "tert-butylimino-tri(pyrrolidino)phosphorane (BTTP)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(OC)c(P(C2CCCCC2)C2CCCCC2)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "BrettPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 0.8999999761581421,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "tert-amyl alcohol"
}
],
"amount": {
"volume": {
"value": 0.10000000149011612,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B23",
"row": "B",
"col": "23"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: BrettPhos Pd G3 / BTTP / 10%tAmOH/NMP; base dispensed in 40% t-AmOH/NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[47] | Record 48 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: tert-butylimino-tri(pyrrolidino)phosphorane (BTTP) REACTANT: OB(O)c1ccccc1 CATALYST: APhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone SOLVENT: tert-amyl alcohol | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[47]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_048"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1"
},
{
"type": "NAME",
"value": "tert-butylimino-tri(pyrrolidino)phosphorane (BTTP)"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1"
},
{
"type": "MDL",
"value": "MFCD00002103"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN(C)c1ccc(P(C(C)(C)C)C(C)(C)C)cc1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "APhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 0.8999999761581421,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "tert-amyl alcohol"
}
],
"amount": {
"volume": {
"value": 0.10000000149011612,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "B24",
"row": "B",
"col": "24"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: APhos Pd G3 / BTTP / 10%tAmOH/NMP; base dispensed in 40% t-AmOH/NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4ccccc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[48] | Record 49 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1cccnc1 CATALYST: XPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4cccnc4 · IDENTITY: — [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4cccnc4 · YIELD: 63.3% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4cccnc4 · AREA: 637049.8 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[48]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_049"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1cccnc1"
},
{
"type": "MDL",
"value": "MFCD00674177"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "XPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "C1",
"row": "C",
"col": "1"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: XPhos Pd G3 / P2-Et / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 55.460723876953125
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4cccnc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "IDENTITY",
"details": "product detected by UPLC-MS ([M+H]+) with a UV peak at the expected retention time"
},
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 63.29999923706055
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 637049.75
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||
| reactions[49] | Record 50 | REACTANT: 2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4) REAGENT: water (added to core stock solution) REAGENT: phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene)) REACTANT: OB(O)c1cccnc1 CATALYST: tBuXPhos Pd G3 (Buchwald precatalyst) SOLVENT: N-methyl-2-pyrrolidone | Not reported | O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4cccnc4 · YIELD: 0% [LCMS] O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4cccnc4 · AREA: 0 [LCMS] | 10.1038/s41586-018-0056-8 |
Decoded fields · reactions[49]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Suzuki-Miyaura cross-coupling"
},
{
"type": "CUSTOM",
"details": "source experiment/sample ID; MOESM3 'Suzuki Coupling Screen 1' (= MOESM9, ED Fig. 6 source data)",
"value": "0378493_0117_050"
}
],
"inputs": {
"aryl halide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Brc1cc(ccn1)c2cc3C(=O)NCCc3[nH]2"
},
{
"type": "NAME",
"value": "2-(2-bromopyridin-4-yl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (4)"
}
],
"amount": {
"moles": {
"value": 100,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water (added to core stock solution)"
}
],
"amount": {
"moles": {
"value": 400,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN=P(N=P(N(C)C)(N(C)C)N(C)C)(N(C)C)N(C)C"
},
{
"type": "NAME",
"value": "phosphazene base P2-Et (1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2lambda5,4lambda5-catenadi(phosphazene))"
}
],
"amount": {
"moles": {
"value": 200,
"units": "NANOMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 4
},
"building block": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1cccnc1"
},
{
"type": "MDL",
"value": "MFCD00674177"
}
],
"amount": {
"moles": {
"value": 150,
"units": "NANOMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 2
},
"precatalyst": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)C(C)(C)C)c(C(C)C)c1.CS(=O)(=O)O[Pd]c1ccccc1-c1ccccc1N"
},
{
"type": "NAME",
"value": "tBuXPhos Pd G3 (Buchwald precatalyst)"
}
],
"amount": {
"moles": {
"value": 10,
"units": "NANOMOLE"
}
},
"reaction_role": "CATALYST"
}
],
"addition_order": 3
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CN1CCCC1=O"
},
{
"type": "NAME",
"value": "N-methyl-2-pyrrolidone"
}
],
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
},
"volume_includes_solutes": true
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "WELL_PLATE",
"details": "1,536-well polypropylene reaction plate (Analytical Sales and Services cat. no. 15020)",
"material": {
"type": "POLYPROPYLENE"
},
"vessel_id": "plate 2",
"position": "C2",
"row": "C",
"col": "2"
},
"is_automated": true,
"automation_platform": "TTP Labtech Mosquito HTS liquid handler",
"environment": {
"type": "GLOVE_BOX",
"details": "MBraun glove box, N2 atmosphere"
}
},
"conditions": {
"temperature": {
"control": {
"type": "AMBIENT"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN"
}
},
"stirring": {
"type": "NONE",
"details": "not stirred; reagents combined by dispense mixing (3 x 750-800 nL) by the liquid handler"
},
"conditions_are_dynamic": false
},
"notes": {
"is_sensitive_to_oxygen": true,
"procedure_details": "Conditions: tBuXPhos Pd G3 / P2-Et / NMP; base dispensed in NMP. Nanomole-scale HTE (SI section 3.1): stock solutions in a 384-well source plate dispensed by a Mosquito HTS into a 1,536-well plate inside an N2 glove box (1 uL reactions, 0.1 M, 100 nmol aryl bromide); core 0.4 M, building block 0.6 M (1.5 equiv), Buchwald precatalyst 0.04 M (10 mol%), base 0.8 M (2 equiv). Plate sealed, centrifuged and left at ambient temperature in the glove box for 18-24 h, then quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl internal standard. Suzuki screen (SI 3.2): 4 equiv H2O added to each core stock; 14 base/solvent combinations (organic bases dispensed in NMP, 40% t-AmOH/NMP or water; K3PO4 and Cs2CO3 in water)."
},
"workups": [
{
"type": "ADDITION",
"details": "Quenched with 3 x 1 uL 0.5 M AcOH in DMSO containing biphenyl (PhPh) internal standard, mixing upon dispense.",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)O"
},
{
"type": "NAME",
"value": "acetic acid (0.5 M in DMSO)"
}
],
"amount": {
"moles": {
"value": 1500,
"units": "NANOMOLE"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(C)=O"
},
{
"type": "NAME",
"value": "DMSO"
}
],
"amount": {
"volume": {
"value": 3,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "biphenyl (PhPh, internal standard)"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "dissolved in the AcOH/DMSO quench solution; concentration not reported"
}
},
"reaction_role": "INTERNAL_STANDARD"
}
]
}
},
{
"type": "ALIQUOT",
"details": "1 uL of the quenched (and, where stated, DMSO-diluted) mixture transferred into 60 uL DMSO in a 384-well analytical plate for UPLC-MS",
"amount": {
"volume": {
"value": 1,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 21,
"precision": 3,
"units": "HOUR"
},
"conversion": {
"value": 0
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1NCCc2[nH]c(cc12)c3ccnc(c3)c4cccnc4"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "YIELD",
"details": "LC-UV estimated yield from the product-to-internal-standard (PhPh) UV peak-area ratio (source column 'Percent Yield'); not isolated",
"uses_internal_standard": true,
"percentage": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
},
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "product UV210 peak area (absolute)",
"float_value": {
"value": 0
},
"wavelength": {
"value": 210,
"units": "NANOMETER"
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY I-class UPLC with PDA and QDa (ESI+) detectors; Cortecs UPLC C18+ 2.1 x 50 mm, 0.1% formic acid water/MeCN, 1 mL/min, 45 C. ",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.1038/s41586-018-0056-8",
"publication_url": "https://doi.org/10.1038/s41586-018-0056-8",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00+00:00"
},
"person": {
"username": "jordan",
"name": "Jordan (Tokens for Progress user; curated with an AI agent)",
"email": "curator@example.org"
}
}
}
} | |||||