These common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: Triazoles
To a flask containing 1-methyl-1H-1,2,3-triazole (430 mg, 0.8 mmol) was added THF (15 mL) and the solution was cooled to -43 C. using a CH3CN-CO2 bath. Then, n-BuLi, (2.5 M in hexanes, 0.7 mL, 1.75 mmol) was added dropwise. The reaction mixture was stirred at -40 C. for 30 minutes, then tert-butyl-3-(4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline-6-carbonyl)-azetidine-1-carboxylate (430 mg, 0.8 mmol, Intermediate 61: step b) in 2 mL THF was introduced. The reaction mixture was allowed to warm to room temperature over 30 minutes, and was quenched after 45 minutes with aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc (3*30 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. Chromatography on Silica gel (10% acetone-hexane increasing to 30% acetone) afforded the title compound as a white amorphous solid. 1H NMR (500 MHz, CDCl3) delta 8.24 (d, J=2.1 Hz, 1H), 7.78 (d, J=8.8 Hz, 1H), 7.56-7.47 (m, 3H), 7.40 (d, J=8.1 Hz, 2H), 7.35 (dd, J=8.7, 2.1 Hz, 1H), 4.35 (s, 2H), 4.20 (t, J=8.8 Hz, 1H), 4.07 (s, 3H), 4.00 (dd, J=9.3, 5.6 Hz, 1H), 3.92 (dd, J=8.9, 5.7 Hz, 1H), 3.67 (s, 3H), 3.62 (t, J=8.8 Hz, 1H), 3.52-3.38 (m, 1H), 1.38 (s, 9H); MS (ESI): mass calcd: Chemical Formula: C30H31ClF3N5O4; Exact Mass: 617.2. m/z found 617.8 [M+H]+.
The synthetic route of 1-Methyl-1H-1,2,3-triazole has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics