New discoveries in chemical research and development in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. name: 1,4-Dimethyl-1H-1,2,3-triazole
(S)-3-Bromo-7-chloro-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H- pyrrolo[2,3-b:4,5-b’]dipyridine (300 mg, 0.657 mmol), l,4-dimethyl-lH-l,2,3-triazole (77 mg, 0.788 mmol), Me4NOAc (87 mg, 0.657 mmol), and PdCl2(PPh3)2 (32.3 mg, 0.046 mmol) were weighed into a vial, and 12 mL NMP was added, and the air was replaced with argon. The sealed reaction vial was heated at 100 C with stirring overnight. The next morning, LC/MS showed the mono-alky lated product as the major peak and a significant amount of the dialkylated product. It was cooled to room temperature and diluted with EtOAc and washed twice with brine. The organic layer was dried over MgS04, and concentrated to obtain a crude mixture. The crude material was purified via preparative LC/MS with the following conditions: Column: XBridge C18, 19 x 200 mm, 5-muiotaeta particles; Mobile Phase A: 5:95 ACN: water with 10-mM NEUOAc; Mobile Phase B: 95:5 ACN: water with 10-mM NH4OAc; Gradient: 20-60% B over 15 min, then a 5- min hold at 100% B; Flow: 20 mL/min. Fractions containing the title compound were combined and dried via centrifugal evaporation. Estimated purity by LC/MS analysis was 99%. An analytical LC/MS injection was used to determine the final purity. Conditions: Column: Waters BEH CI 8, 2.0 x 50 mm, 1.7-muiotaeta particles; Mobile Phase A: 5:95 ACN:water with 10 mM NH4OAc; Mobile Phase B: 95:5 ACN:water with 10 mM NH4OAc; Temperature: 50 C; Gradient: 0%B, 0-100% B over 3 min, then a 0.5-min hold at 100% B; Flow: 1 mL/min; Detection: UV at 220 nm; RT = 1.51 min, LC/MS (M+H) = 534.5. NMR (500MHz, DMSO-c e) delta 8.82 (d, J=8.1 Hz, 1H), 8.67 (s, 1H), 8.57 (br. s., 1H), 7.77 – 7.71 (m, 3H), 7.35 – 7.29 (m, 2H), 7.27 – 7.21 (m, 1H), 6.06 (br. s., 1H), 4.38 (s, 3H), 4.03 (s, 3H), 3.90 (s, 1H), 3.74 (d, J=10.6 Hz, 1H), 3.62 (br. s., 1H), 3.40 (s, 1H), 3.24 (t, J=11.2 Hz, 1H), 2.54 (s, 3H), 2.31 (s, 3H), 1.62 (br. s., 1H), 1.51 – 1.39 (m, 1H), 1.35 – 1.21 (m, 1H), 1.14 (d, J=12.5 Hz, 1H); LC/MS (M+H) = 534.3 [Column: Waters Aquity BEH CI 8 2.1 X 50 mm 1.7u; Mobile Phase A: water with 0.05% TFA; Mobile Phase B: ACN with 0.05% TFA; Temperature: 40 C; Gradient: 2- 98% B over 1.5 min; Flow: 0.8 mL/min].
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Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; VACCARO, Wayne; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; DELUCCA, George V.; DESKUS, Jeffrey A.; HAN, Wen-Ching; KUMI, Godwin Kwame; SCHMITZ, William D.; STARRETT, John E., JR.; HILL, Matthew D.; HUANG, Hong; (563 pag.)WO2016/183118; (2016); A1;,
1,2,3-Triazole – Wikipedia,
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