{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0b96b962765f4cca8835ec98c058a5a4","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"7a4384e338f6fba52057e894cdca503467ded0a638130e129746500b881e7174","doi":"10.1002/anie.201907366","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-14011173ac082dda","route_slugs":["ord-0b96b962765f4cca8835ec98c058a5a4-a58301918df2"],"reactant_slugs":["ord-compound-3b6484b9fe70f2c32497"],"product_slugs":["ord-compound-9fb6d28c1756751bc99a"],"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_831"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(NCC=1C=CC=CC1)C2=CC=C(C=C2)C(F)(F)F"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"365274-70-0"}],"amount":{"moles":{"value":0.6,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C[OH2+].C[OH2+].C1CC=CCCC=C1.C1CC=CCCC=C1.[Ir].[Ir]"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"12148-71-9"}],"amount":{"moles":{"value":0.009,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(NC1=CC=CC2=C1NC(=C2C)C)C=3C=NC(=CC3)C4=NC=CC=C4"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"2366213-69-4"}],"amount":{"moles":{"value":0.0198,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"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"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O1CCCC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"109-99-9"}],"amount":{"volume":{"value":3,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":60,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"notes":{"procedure_details":"Isolated by chromatography using deactivated silica gel and ethyl acetate and petroleum ether (10:1 to 1:1) as the eluent."},"outcomes":[{"reaction_time":{"value":96,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(NCC=1C=CC=CC1)C2=CC=C(C=C2B3OC(C)(C)C(O3)(C)C)C(F)(F)F"},{"type":"CAS_NUMBER","value":"2366213-95-6"}],"measurements":[{"analysis_key":"MS of product_1","type":"IDENTITY"},{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":40}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (500 MHz, CDCl3) δ 8.67 (s, 1H, amide-NH), 7.94 (d, J = 8.3 Hz, 1H, Ha), 7.87 (s, 1H, Hc), 7.57 – 7.56 (m, 2H), 7.36 – 7.22 (m, 4H), 4.29 (d, J = 5.5 Hz, 2H, Bn-CH2), 1.28 (s, 12H, pin-Me). 13C NMR (126 MHz, CDCl3) δ 169.66, 138.63, 136.50, 133.83 (m, two bonds C-F coupling), 128.95 (m, three bond C-F coupling), 128.77, 128.15, 128.01, 126.19 (m, one bond C-F coupling), 125.59 (m, three bond C-F coupling), 124.79, 82.89, 45.01, 24.99."}}},"MS of product_1":{"type":"HRMS","details":"HRMS Found: 405.1743","data":{"found":{"float_value":405.1743,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1002/anie.201907366"}}},"entities":[{"slug":"ord-compound-3b6484b9fe70f2c32497","name":"C15H12F3NO · ORD MVMBCPQNHHXPIH-UHFFFAOYSA-N","smiles":"O=C(NCc1ccccc1)c1ccc(C(F)(F)F)cc1","inchi":"InChI=1S/C15H12F3NO/c16-15(17,18)13-8-6-12(7-9-13)14(20)19-10-11-4-2-1-3-5-11/h1-9H,10H2,(H,19,20)","formula":"C15H12F3NO"},{"slug":"ord-compound-9fb6d28c1756751bc99a","name":"C21H23BF3NO3 · ORD WNSNMCNLWZNKKE-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2cc(C(F)(F)F)ccc2C(=O)NCc2ccccc2)OC1(C)C","inchi":"InChI=1S/C21H23BF3NO3/c1-19(2)20(3,4)29-22(28-19)17-12-15(21(23,24)25)10-11-16(17)18(27)26-13-14-8-6-5-7-9-14/h5-12H,13H2,1-4H3,(H,26,27)","formula":"C21H23BF3NO3"}],"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-14011173ac082dda","title":"Literature experiment — 10.1002/anie.201907366","source_type":"paper","doi":"10.1002/anie.201907366","url":"https://doi.org/10.1002/anie.201907366","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"]}