{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-061a7ea6016048c1bd19d5920926e678","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"225867506e96eb15036cc19adb8734914df531fdc6d3a00d1ffa2e2d64d75b91","doi":"10.1002/anie.201708967","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-c772e94b40b29614","route_slugs":["ord-061a7ea6016048c1bd19d5920926e678-eb93610fa0b3","ord-061a7ea6016048c1bd19d5920926e678-640caad5145e"],"reactant_slugs":["ord-compound-412020cc0b4ea3f4173c"],"product_slugs":["ord-compound-5ce8189430834abd7183","ord-compound-478ca184161229c80531"],"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_473"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(NCCC=1C=CC=C(F)C1)C(F)(F)F"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1465429-93-9"}],"amount":{"moles":{"value":0.25,"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":0.00375,"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":0.5,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O=S(=O)([O-])CC=1C=NC(=CC1)C2=NC=C(C=C2)C.CCCC[N+](CCCC)(CCCC)CCCC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"2007932-96-7"}],"amount":{"moles":{"value":0.0075,"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":1.25,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":50,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"ARGON"}},"stirring":{}},"notes":{"procedure_details":"Following general procedure F using 4e (58.8 mg, 0.25 mmol), B2pin2 (127 mg, 0.50 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and 1a (3.8 mg, 0.0075 mmol) in THF (1.25 mL). Stirred in vial at 50 °C for 20 hours. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 12.9:1 meta:para borylation in 98% yield (these numbers include some meta isomer that has also undergone NH borylation). The crude product was purified by silica gel chromatography (15% EtOAc in Petroleum Ether 40‐60 o C) which resulted in the cleavage of the N‐B bond in the NH‐borylation material and gave the title compound (as a 13:1 mixture of meta:para ratio, as determined by 1 H NMR) as a white solid (80 mg, 0.22 mmol, 89%)."},"outcomes":[{"reaction_time":{"value":20,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(NCCC=1C=C(F)C=C(C1)B2OC(C)(C)C(O2)(C)C)C(F)(F)F"},{"type":"CAS_NUMBER","value":"2135636-92-7"}],"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":83}}],"reaction_role":"PRODUCT"},{"identifiers":[{"type":"SMILES","value":"O=C(NCCC1=CC=C(B2OC(C)(C)C(O2)(C)C)C(F)=C1)C(F)(F)F"},{"type":"CAS_NUMBER","value":"2135636-93-8"}],"measurements":[{"analysis_key":"product_2_UNKNOWN","type":"YIELD","percentage":{"value":6}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"Meta 1 H NMR (600 MHz, CDCl3) δ 7.41 (s, 1H), 7.36 (dd, J = 8.7, 2.3 Hz, 1H), 6.97 (d, J = 9.3 Hz, 1H), 6.68 (br, 1H), 3.60 (dt, J = 6.9, 6.5 Hz, 2H), 2.88 (t, J = 7.2 Hz, 2H), 1.34 (s, 12H); 13C NMR (151 MHz, CDCl3) δ 162.7 (d, J = 247.6 Hz), 157.3 (q, J = 37.0 Hz), 139.5 (d, J = 6.6 Hz), 130.6 (d, J = 2.5 Hz), 119.5 (d, J = 19.3 Hz), 118.4 (d, J = 21.3 Hz), 115.7 (q, J = 287.7 Hz), 84.2, 40.8, 34.5, 24.8.; Para 1 H NMR (600 MHz, CDCl3) δ 7.72 – 7.64 (m, 1H), 6.97 (d, J = 8.6 Hz, 1H), 6.87 (m, 1H), 6.69 (br, 1H), 3.68 – 3.49 (m, 2H), 2.88 (m, 2H), 1.35 (s, 12H); 13C NMR (151 MHz, CDCl3) δ 167.4 (d, J = 251.7 Hz), 157.3 (q, J = 37.1 Hz), 143.8 (d, J = 8.2 Hz), 137.3 (d, J = 8.6 Hz), 130.6 (d, J = 2.6 Hz), 124.1 (d, J = 2.8 Hz), 115.5 (d, J = 24.1 Hz), 84.0, 40.6, 34.7, 24.8."}}},"MS of product_1":{"type":"HRMS","details":"HRMS Expected: 362.1554 Found: 362.1552","data":{"expected":{"float_value":362.1554,"description":"Expected m/z"},"found":{"float_value":362.1552,"description":"Observed m/z"}}},"product_2_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"}}}],"provenance":{"doi":"10.1002/anie.201708967"}}},"entities":[{"slug":"ord-compound-412020cc0b4ea3f4173c","name":"C10H9F4NO · ORD BALKMMYOCJAUEO-UHFFFAOYSA-N","smiles":"O=C(NCCc1cccc(F)c1)C(F)(F)F","inchi":"InChI=1S/C10H9F4NO/c11-8-3-1-2-7(6-8)4-5-15-9(16)10(12,13)14/h1-3,6H,4-5H2,(H,15,16)","formula":"C10H9F4NO"},{"slug":"ord-compound-5ce8189430834abd7183","name":"C16H20BF4NO3 · ORD XJXZEUWDGPLNHG-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2cc(F)cc(CCNC(=O)C(F)(F)F)c2)OC1(C)C","inchi":"InChI=1S/C16H20BF4NO3/c1-14(2)15(3,4)25-17(24-14)11-7-10(8-12(18)9-11)5-6-22-13(23)16(19,20)21/h7-9H,5-6H2,1-4H3,(H,22,23)","formula":"C16H20BF4NO3"},{"slug":"ord-compound-478ca184161229c80531","name":"C16H20BF4NO3 · ORD NLECBTQVPKXXQZ-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2ccc(CCNC(=O)C(F)(F)F)cc2F)OC1(C)C","inchi":"InChI=1S/C16H20BF4NO3/c1-14(2)15(3,4)25-17(24-14)11-6-5-10(9-12(11)18)7-8-22-13(23)16(19,20)21/h5-6,9H,7-8H2,1-4H3,(H,22,23)","formula":"C16H20BF4NO3"}],"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-c772e94b40b29614","title":"Literature experiment — 10.1002/anie.201708967","source_type":"paper","doi":"10.1002/anie.201708967","url":"https://doi.org/10.1002/anie.201708967","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"]}