Electric Literature of 16681-72-4, New Advances in Chemical Research in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 16681-72-4, name is 5-Bromo-1-methyl-1H-1,2,4-triazole, molecular formula is C3H4BrN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.
Example 245. 4-(2-(l-(3-Chloro-2-fluorophenyl)-lH-l,2,3-triazole-4-carbonyl)- 5-(l -methyl- 1H- 1 ,2,4-triazol-5-yl)- 1 ,2,3 ,4-tetrahydroisoquinoline- 1 -carboxamido) benzoic acid, TFA salt: Intermediate 44 (0.050 g, 0.071 mmol), 5-bromo-l -methyl- 1H- 1,2,4-triazole (0.017 g, 0.107 mmol), and Na2C03 (2.0M aq. solution) (0.178 mL, 0.356 mmol) were added to dioxane (1.0 mL) and degassed for 15 min. Tetrakis (triphenylphosphine)palladium(O) (8.23 mg, 7.12 muiotaetaomicron) was added and the mixture was irradiated at 120 C for 15 min. The reaction mixture was poured into EtOAc, washed with saturated aHC03 solution, brine, dried over sodium sulfate, filtered, and concentrated. The /-butyl ester group was removed was treatment with 50% TFA/DCM, concentrated, purified by reverse phase prep. HPLC, and freeze-dried to give the title compound as a white solid (14.3 mg, 27%). NMR (400MHz, DMSO-d6) delta 11.02 (s, 1H), 9.21 – 9.15 (m, 1H), 8.14 – 8.05 (m, 1H), 7.93 – 7.84 (m, 5H), 7.75 (d, J = 8.8 Hz, 2H), 7.54 – 7.45 (m, 3H), 6.05 (s, 1H), 4.51 – 4.40 (m, 1H), 4.19 (ddd, J = 12.7, 8.3, 4.2 Hz, 1H), 3.76 (s, 3H), 3.11 – 3.02 (m, 1H), 2.91 – 2.81 (m, 1H) ppm. MS (ESI) m/z: 601(M+H)+. Analytical HPLC: RT = 6.14 min (Method B).
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Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.P.; CLARK, Charles G.; SMITH, II, Leon M.; ORWAT, Michael J.; JEON, Yoon; CORTE, James R.; WO2014/160668; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics