A common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, 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. 16681-65-5.
Example 93: (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(3,5-dimethylisoxazol-4-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol To a flask containing 1 -methyl- lH-1, 2, 3-triazole (200 mg, 2.41 mmol) was added THF (17 mL) and the solution was cooled to -43 C using a CH3CN-CQ2bath. -BuLi, (2,5 M in hexanes, 0.88 mL, 2.19 mmol) was then added dropwise to provide a white suspension. The suspension was stirred at -40 C for 20 minutes, then a homogeneous solution of (4-chloro-2-methoxy-3-(4- (trifluoromethyl)benzyl)quinolii^ (500 mg, 1.05 mmol, Intermediate 63: step b) in 2 ml, TFIF was introduced. A dark brownish solution immediately resulted. The reaction mixture was allowed to warm gradually to 0 C over 25 minutes, then was quenched with aqueous H4CI solution. The aqueous portion was extracted with EtOAc (3 x 35 mL) and the combined organics were washed with brine, dried over MgS04, filtered and concentrated to dryness. The residue was purified by FCC (20% EtOAc-hexanes increasing to 50% EtOAc) to provide the title compound as a white solid. H NMR (500 MHz,CDC ) delta 8.08 (d, J —— 2.1 Hz, 1 H), 7.85 (d, J —— 8.7 Hz, IH), 7.61 – 7.46 (m, 3H), 7.39 (d, J —— 8.1Hz, 2H), 6.94 (s, IH), 4.81 (s, IH), 4.32 (s, 2H), 4.09 (s, 3H), 3.98 (s, 3H), 1.95 (s, 3H), 1.82 (s, 3H); MS (ESI): mass calc. for Chemical Formula: C27H23CIF3N5Q3; Exact Mass: 557.1, m z found, 557.9 (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; WO2015/57205; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics