{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-092edf7c2a86407abc9c399fec1a8813","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"116925ef20e9f1a9853850a8c52824e8c9b2e19cc6e9c3ad01c281da96afb41e","doi":"10.1002/anie.201509996","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-815566de10ae9f13","route_slugs":["ord-092edf7c2a86407abc9c399fec1a8813-0a8c13dddeca"],"reactant_slugs":["ord-compound-3cb86442d15e0266e2d1"],"product_slugs":["ord-compound-4955fe9dd4358f6bef63"],"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_850"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"reagent_5":{"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":0.2,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(NC1=C(F)C(F)=C(C(F)=C1F)C(F)(F)F)C(C)(C)CCCOC2=CC(=CC=C2C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1257521-31-5"}],"amount":{"moles":{"value":0.1,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"reagent_4":{"components":[{"identifiers":[{"type":"SMILES","value":"[K].O=C(O)O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"298-14-6"}],"amount":{"moles":{"value":0.2,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N#CC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"75-05-8"}],"amount":{"volume":{"value":1.4999925,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"reagent_3":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1C(OC)=CC(OC)=C2C=CC=CC12"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"40335-00-0"}],"amount":{"moles":{"value":0.02,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"[Pd].O=C(O)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"3375-31-3"}],"amount":{"moles":{"value":0.01,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(O)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"64-19-7"}],"amount":{"moles":{"value":0.02,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"[B-](F)(F)(F)F.CC[N+](CC)(CC)CC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"429-06-1"}],"amount":{"moles":{"value":0.05,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"OXYGEN"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":15,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(NC1=C(F)C(F)=C(C(F)=C1F)C(F)(F)F)C(C)(CB2OC(C)(C)C(O2)(C)C)CCCOC3=CC(=CC=C3C)C"},{"type":"CAS_NUMBER","value":"1835284-27-9"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":71}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1 H NMR (400 MHz, CDCl3) δ 8.48 (br s, 1H), 6.98 (d, J = 7.6 Hz, 1H), 6.65-6.61 (m, 2H), 4.01-3.89 (m, 2H), 2.30 (s, 3H), 2.15 (s, 3H), 1.96-1.78 (m, 4H), 1.41-1.35 (m, 4H), 1.28-1.18 (s, 13H).; 13 C NMR (100 MHz, CDCl3) δ 175.8, 156.8, 136.5, 130.2, 123.4, 120.7, 112.0, 84.2, 67.7, 44.6, 38.5, 25.8, 24.9, 24.75, 24.70, 21.4, 15.7."}}}}}],"provenance":{"doi":"10.1002/anie.201509996"}}},"entities":[{"slug":"ord-compound-3cb86442d15e0266e2d1","name":"C22H22F7NO2 · ORD FCQNPSRIBVPIPR-UHFFFAOYSA-N","smiles":"Cc1ccc(C)c(OCCCC(C)(C)C(=O)Nc2c(F)c(F)c(C(F)(F)F)c(F)c2F)c1","inchi":"InChI=1S/C22H22F7NO2/c1-11-6-7-12(2)13(10-11)32-9-5-8-21(3,4)20(31)30-19-17(25)15(23)14(22(27,28)29)16(24)18(19)26/h6-7,10H,5,8-9H2,1-4H3,(H,30,31)","formula":"C22H22F7NO2"},{"slug":"ord-compound-4955fe9dd4358f6bef63","name":"C28H33BF7NO4 · ORD FTTRWBOUOUIEMU-UHFFFAOYSA-N","smiles":"Cc1ccc(C)c(OCCCC(C)(CB2OC(C)(C)C(C)(C)O2)C(=O)Nc2c(F)c(F)c(C(F)(F)F)c(F)c2F)c1","inchi":"InChI=1S/C28H33BF7NO4/c1-15-9-10-16(2)17(13-15)39-12-8-11-27(7,14-29-40-25(3,4)26(5,6)41-29)24(38)37-23-21(32)19(30)18(28(34,35)36)20(31)22(23)33/h9-10,13H,8,11-12,14H2,1-7H3,(H,37,38)","formula":"C28H33BF7NO4"}],"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-815566de10ae9f13","title":"Literature experiment — 10.1002/anie.201509996","source_type":"paper","doi":"10.1002/anie.201509996","url":"https://doi.org/10.1002/anie.201509996","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"]}