{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-1d47764836bc48998408c231e6f9c3c9","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"18b256fd5a264624a1a784302619342803a15385b5e377a2acfca040d93fe60c","doi":"10.1021/jacs.0c05434","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-94f4664d96137ccc","route_slugs":["ord-1d47764836bc48998408c231e6f9c3c9-830928be3a8d"],"reactant_slugs":["indole"],"product_slugs":["ord-compound-607ed1070e8192293eb3"],"selection_notes":["Only explicitly marked REACTANT inputs become graph starting points.","Only products with a positive reported numeric YIELD become graph destinations; all reported outcomes remain in raw.","One representative record per exact reactant/product structure set; other conditions are not additional transformations."],"raw":{"identifiers":[{"type":"CUSTOM","details":"rxn_id from SURF table","value":"lit_pub_bo_139"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"[Ni](=C1N(C=CN1C=2C(=CC(=CC2C)C)C)C=3C(=CC(=CC3C)C)C)=C4N(C=CN4C=5C(=CC(=CC5C)C)C)C=6C(=CC(=CC6C)C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"155519-31-6"}],"amount":{"moles":{"value":0.02,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"73183-34-3"}],"amount":{"moles":{"value":0.3,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C=1C=CC=2NC=CC2C1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"120-72-9"}],"amount":{"moles":{"value":0.2,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C=1C=CC(=CC1)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"108-88-3"}],"amount":{"volume":{"value":1,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":60,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"ARGON"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":4,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)C2=CNC=3C=CC=CC32"},{"type":"CAS_NUMBER","value":"937366-54-6"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_MS","type":"YIELD","percentage":{"value":30}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1 H NMR (500 MHz, C6D6): δ 8.36-8.33 (m, 1H), 7.63-7.61 (m, 1H), 7.56 (d, J = 3 Hz, 1H), 7.33-7.30 (m, 1H), 7.23-7.20 (m, 1H), 6.57 (dd, J = 1 Hz, J = 3 Hz, 1H), 1.02 (s, 12H).; 13 C NMR (126 MHz, C6D6): δ 139.7, 131.6, 128.8, 122.9, 121.6, 120.7, 114.8, 107.5, 83.9, 24.2.; 11 B NMR (160 MHz, C6D6): δ 24.7."}}},"product_1_MS":{"type":"MS","details":"MS"}}}],"provenance":{"doi":"10.1021/jacs.0c05434"}}},"entities":[{"slug":"indole","name":"Indole","smiles":"C1=CC=C2C(=C1)C=CN2","inchi":"InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H","formula":"C8H7N"},{"slug":"ord-compound-607ed1070e8192293eb3","name":"C14H18BNO2 · ORD WQPRSRMWYVTUTE-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2c[nH]c3ccccc23)OC1(C)C","inchi":"InChI=1S/C14H18BNO2/c1-13(2)14(3,4)18-15(17-13)11-9-16-12-8-6-5-7-10(11)12/h5-9,16H,1-4H3","formula":"C14H18BNO2"}],"dataset":{"dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","name":"Borylation dataset from Roche","description":"Borylation reactions which were extracted from the literature by Roche scientists and published in the SURF format (ChemRxiv, 2024, DOI: 10.26434/chemrxiv-2023-nfq7h)","records_in_source":1111,"path":"data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet","sha256":"e01a389cac3e6cce5746ef54dbe6b8d3040d764f987b1fc13790f5aeff5598fa","bytes":210626,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet"},"publication":{"slug":"ord-publication-94f4664d96137ccc","title":"Literature experiment — 10.1021/jacs.0c05434","source_type":"paper","doi":"10.1021/jacs.0c05434","url":"https://doi.org/10.1021/jacs.0c05434","note":"Publication DOI reported by the Open Reaction Database. Experimental record data adapted under CC BY-SA 4.0; https://creativecommons.org/licenses/by-sa/4.0/"},"license":"CC-BY-SA-4.0","license_url":"https://creativecommons.org/licenses/by-sa/4.0/","attribution":"Open Reaction Database contributors and the cited original publications","changes":["Bounded selection across datasets and publications","Deduplicated exact transformations across conditions","Canonicalized molecular structures using RDKit; calculated identifiers, formulae and molecular weights","Explicitly incomplete directed branches for all recorded reactants and positively measured products","Removed submitter account and contact fields from provenance; retained scientific input and outcome fields"]}