Extracurricular laboratory: Synthetic route of Methyl 5-bromo-1H-imidazole-4-carboxylate

According to the analysis of related databases, 1093261-46-1, the application of this compound in the production field has become more and more popular.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1093261-46-1, name is Methyl 5-bromo-1H-imidazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl 5-bromo-1H-imidazole-4-carboxylate

A solution of methyl 4-bromo-1 /-/-imidazole-5-carboxylate (0.708 g, 3.5 mmol) was stirred in a solution of MeOH (20 mL) and 2N NaOH (20 mL, 40 mmol) at 40 0C for 4h, then additional 2N NaOH (20 mL, 40 mmol) was added and the reaction mixture kept at 40 0C for another hour. The reaction mixture was then acidified by addition of 1 M HCI (100 mL) and extracted with EtOAc. The organic extracts were dried (Na2SO4), and the solvent was evaporated to provide crude 4-bromo-1 /-/-imidazole-5- carboxylic acid (0.156g, 24%) as a white solid which was used without further purification.4-Bromo-lambda/-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1 /-/- imidazole-5-carboxamide trifluoroacetate was prepared in a similar manner as described herein from 3-{[3-aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5- chlorobenzonitrile (0.062 g, 0.20 mmol), 4-bromo-1 /-/-imidazole-5-carboxylic acid (0.038 g, 0.20 mmol), HATU (0.091 g, 0.24 mmol), DIPEA (0.042 ml_, 0.24 mmol) and DMF (2 ml_). Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA) to afford the title compound (0.010 g, 8%) as a white solid. 1H NMR (400 MHz, DMSOd6) delta ppm 8.38 (br. s., 1 H), 7.82 (s, 2 H), 7.44 – 7.54 (m, 3 H), 7.38 (t, 1 H), 4.51 (d, 2 H). ES-LCMS: m/z 482.9, 484.9, 486.9 (M+1 ).

According to the analysis of related databases, 1093261-46-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/154271; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem