{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-04ef4005b699487e9a1d97d3cb0cd4bf","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"77f6553bb196d0abd762bd24525e917b133a86aae591a0d0b1943baf35428bff","doi":"10.1002/anie.201104544","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-1d9db24d746d4eac","route_slugs":["ord-04ef4005b699487e9a1d97d3cb0cd4bf-88f3c91987f6"],"reactant_slugs":["ord-compound-e1b7767b8ce2fafa1bf3"],"product_slugs":["ord-compound-339839d0a8041e78c1e8"],"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_1301"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"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":1,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N(=CC1=CC=CC=2C=CC=CC12)N(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"59670-84-7"}],"amount":{"moles":{"value":0.5,"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":0.0025,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O1BOC(C)(C)C1(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"25015-63-8"}],"amount":{"moles":{"value":0.025,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1C=CC=CC1C=NN(CC=2C=CC=CC2)CC=3C=CC=CC3"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"237402-29-8"}],"amount":{"moles":{"value":0.005,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_3":{"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":0.5,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"ARGON"}},"stirring":{}},"notes":{"procedure_details":"Following the general procedure, column chromatography in neutral alumina (EtOAc/n-hexane 1:8) afforded 11i (155 mg, 95 %) as a yellow oil."},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"N(=CC1=C(C=CC=2C=CC=CC21)B3OC(C)(C)C(O3)(C)C)N(C)C"},{"type":"CAS_NUMBER","value":"1360607-22-2"}],"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":95}}],"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 8.77-8.76 (m, 1H), 8.31 (s, 1H,), 7.79-7.78 (m, 1H) 7.75 (d, 1H, J = 10.5 Hz), 7.71 (d, 1H, J = 10.5 Hz), 7.49-7.47 (m, 2H), 3.07 (s, 6H), 1.39 (s, 12H). 13C NMR (125 MHz, CDCl3): δ 139.4, 135.4, 135.1, 130.6, 128.1, 126.7, 126.3, 126.3, 125.9, 83.6, 42.9, 25.0 (C-B not observed); 11B NMR (160 MHz, CDCl3): δ 32.2 ppm;"}}},"MS of product_1":{"type":"HRMS","details":"HRMS Found: 324.2017","data":{"found":{"float_value":324.2017,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1002/anie.201104544"}}},"entities":[{"slug":"ord-compound-e1b7767b8ce2fafa1bf3","name":"C13H14N2 · ORD DFEZHELNRPACHC-UHFFFAOYSA-N","smiles":"CN(C)N=Cc1cccc2ccccc12","inchi":"InChI=1S/C13H14N2/c1-15(2)14-10-12-8-5-7-11-6-3-4-9-13(11)12/h3-10H,1-2H3","formula":"C13H14N2"},{"slug":"ord-compound-339839d0a8041e78c1e8","name":"C19H25BN2O2 · ORD OZRMFWAMCXLUTR-UHFFFAOYSA-N","smiles":"CN(C)N=Cc1c(B2OC(C)(C)C(C)(C)O2)ccc2ccccc12","inchi":"InChI=1S/C19H25BN2O2/c1-18(2)19(3,4)24-20(23-18)17-12-11-14-9-7-8-10-15(14)16(17)13-21-22(5)6/h7-13H,1-6H3","formula":"C19H25BN2O2"}],"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-1d9db24d746d4eac","title":"Literature experiment — 10.1002/anie.201104544","source_type":"paper","doi":"10.1002/anie.201104544","url":"https://doi.org/10.1002/anie.201104544","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"]}