Category: 202931-88-2

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

Application of 202931-88-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 202931-88-2, name is 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

-78 in hexane ofn-butyllithium solution (1.6 M, 0.71 mL, 1.1 mmol) in tetrahydrofuran (11 mL) of 3 – (4 – (1H-pyrazol-1- yl) benzyl) -6 – bromo-4-chloro-2-methoxy-quinoline (490 mg, 1.1 mmol, intermediate 4: step d) of stirring the solution was added dropwise.After two minutes, tetrahydrofuran (1 mL) of 1-methyl -1H- 1, 2,3-triazole-5-carbaldehyde (140 mg, 1.1 mmol, Intermediate 18). After 5 minutes, the flask was placed in an ice water bath.After 1 hour, water was added (10 mL) and ethyl acetate (60 mL).The two phase mixture was stirred for 10 min.By the addition of half saturated aqueous sodium chloride solution (50 mL), the layers were separated.The organic layer was dried over sodium sulfate, filtered, the solution dried.Addition of silica gel (4 g) to the filtrate, the mixture was concentrated by rotary evaporation to give a free-flowing powder.Powder was loaded onto a silica gel column for flash column chromatography purification.Initially with 100% hexane and eluted by a grading to 100% ethyl acetate to give the title compound as an impure white foam.Suspending the foam in methanol (20 mL) and then the suspension was sonicated for 5 minutes.Collect the solid by filtration, and rinsed with methanol (5 mL).The combined solids dried to a white solid as the title compound was obtained.

The synthetic route of 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceuticals N.V; Leonardo, Christi.A.; Barvei, Kent; Edward, James P.; Gloita, Kevin D.; Kummer, David .A.; Maharoof, Umar; Nishimura, Rachael; Urbanski, Mode; Venkatesan, Hariharan; Wang, Ai Hua; Olin, Ronald L.; Woods, Craig; Fourier, Anne; Shu, Jih; Cumings, Maxwell D.; (86 pag.)KR2016/68948; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics