Application of 1003-21-0, 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. 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.
Ethylmagnesium bromide (3 M in Et2O, 0.0642 mL, 0.193 mmol) was added dropwise to a solution of 5-bromo-1-methyl-1H-imidazole (31.0 mg, 0.193 mmol) in DCM (1 mL) under a nitrogen atmosphere. The mixture was stirred at room temperature for 15 min, then was cooled to 0 C. A solution of (2,4-dichloro-3-phenylquinolin-6-yl)(3-methylisoxazol-5-yl)methanone (49.2 mg, 0.128 mmol, Intermediate 37, step b) in DCM (2 mL) was added via cannula. The mixture was stirred at room temperature for 2 hours. The reaction was quenched by addition of saturated aqueous NH4Cl and was diluted with water. The mixture was extracted three times with EtOAc. The organic phase was dried (Na2SO4), filtered, and concentrated. The crude product was purified by RP-HPLC (10-90% CH3CN-H2O, 0.1% TFA) to afford the title compound. 1H NMR (400 MHz, DMSO-d6) delta 8.99 (br. s., 1H), 8.39 (s, 1H), 8.10-8.25 (m, 2H), 7.83 (d, J=9.05 Hz, 1H), 7.47-7.63 (m, 3H), 7.36-7.47 (m, 2H), 7.27 (br. s., 1H), 6.38 (s, 1H), 3.52 (s, 3H), 2.24 (s, 3H); MS m/e 465.1 [M+H]+.
The synthetic route of 5-Bromo-1-methyl-1H-imidazole 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; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem