Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 202931-88-2, name is 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde, A new synthetic method of this compound is introduced below., name: 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde
To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (1.45 g, 3.37 mmol, Intermediate 10: step d) was added THF (25 mL) and the solution was cooled to -75 C. n-BuLi (2.5 M in hexanes, 1.3 mL, 3.25 mmol) was added dropwise. After 2 minutes, 1-methyl-1H-1,2,3-triazole-5-carbaldehyde (580 mg, 5.22 mmol, Intermediate 18) in 3 mL THF was introduced. The reaction mixture was allowed to warm to -20 C. over 45 minutes at which time the reaction was quenched with aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc (5*40 mL) and the combined organics were washed with brine, dried over MgSO4, filtered and concentrated. Chromatography on silica gel (5% CH3CN-DCM increasing to 30% CH3CN +2% MeOH) afforded the title compound as an off white amorphous solid. 1H NMR (600 MHz, CDCl3) delta 8.15 (d, J=1.9 Hz, 1H), 7.82 (d, J=8.6 Hz, 1H), 7.54 (dd, J=8.6, 2.0 Hz, 1H), 7.49 (d, J=8.2 Hz, 2H), 7.38 (d, J=8.1 Hz, 2H), 7.27 (s, 1H), 6.14 (d, J=4.6 Hz, 1H), 5.01 (s, 1H), 4.33 (s, 2H), 4.07 (s, 3H), 3.95 (s, 3H). MS (ESI): mass calcd. for C22H18ClF3N4O2, 462.1, m/z found 463.1 [M+H]+.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
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.; US2015/105372; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics