{
  "source": "ORD Dataset Wishlist",
  "snapshot_date": "2026-09-25",
  "ord_wishlist_status_at_snapshot": "Available",
  "ord_wishlist_card": "https://github.com/orgs/open-reaction-database/projects/11?pane=issue&itemId=126570034",
  "ord_data_issue": null,
  "title": "End-to-End Automated Synthesis of C(sp3)-Enriched Drug-like Molecules via Negishi Coupling and Novel, Automated Liquid–Liquid Extraction",
  "doi": "10.1021/acs.jmedchem.2c01646",
  "journal": "J Med Chem",
  "publication_date": "2022-12-15",
  "authors": [
    "Irini Abdiaj",
    "Santiago Cañellas",
    "Alejandro Diéguez-Vázquez",
    "María Lourdes Linares",
    "Brenda Pijper",
    "Alberto Fontana",
    "Raquel Rodríguez",
    "Andrés A. Trabanco",
    "Eduardo Palao",
    "Jesús Alcázar"
  ],
  "article_open_access": {
    "status": "hybrid",
    "license": "cc-by-nc-nd"
  },
  "dataset_size_estimate": null,
  "experiment_type": null,
  "ord_priority": null,
  "ord_difficulty": null,
  "source_data_kind": "author_request_needed",
  "smiles_in_source": "unknown",
  "needs_author_contact": true,
  "data_locations": [
    {
      "url": "https://doi.org/10.1021/acs.jmedchem.2c01646",
      "what": "J. Med. Chem. article and ACS-hosted SI (experimental procedures/characterization)",
      "license": "Article CC-BY-NC-ND 4.0 per Crossref; SI license not verified"
    },
    {
      "url": "https://zenodo.org/records/7842092",
      "what": "Pre-peer-review manuscript PDF (1.5 MB): Table 1 combinatorial indazole library (LC-MS conversions), a 54-reaction sequential stability run (figure), procedures; no raw data files",
      "license": "CC-BY 4.0 (Zenodo record)"
    }
  ],
  "notes": "Source: Abdiaj et al., J. Med. Chem. 2023, 66, 716 (online Dec 2022), doi:10.1021/acs.jmedchem.2c01646. The article is CC-BY-NC-ND 4.0, and a CC-BY 4.0 pre-review manuscript is on Zenodo (record 7842092). The workflow runs automated sequential organozinc generation from alkyl halides in flow, then Pd-catalyzed Negishi coupling, automated liquid-liquid extraction and mass-triggered prep HPLC. The full automated-run data is not in the paper and would need to be released by the authors. The published material holds only a combinatorial library table (LC-MS conversions), a 54-reaction sequential stability run shown as a plot, and compound procedures. Pitfalls: this is a multi-step flow process (packed Zn column organozinc formation feeding the coupling). Conversions are LC-MS-based relative to identified by-products, while other values are assay yields with an internal standard; keep these measurement types distinct.",
  "verification_caveats": "Multi-step telescoped flow (organozinc formation plus coupling plus automated workup). Outcomes mix LC-MS conversion and assay yield. The stability series is only in a figure. Without the released data, a dataset would cover only the published scope table."
}