Synthetic Route of 1003-21-0,Some common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, 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.
To a mixture of 5-bromo-1-methyl-1H-imidazole (569 mg, 3.417 mmol) in THF (14 mL) at 0 C. was added iPrMgCl-LiCl (1.3 M in THF, 2.48 mL, 3.22 mmol) to provide a white suspension. This mixture was stirred at 0 C. for 10 minutes, then the ice-water bath was removed and the mixture stirred at room temperature for 10 minutes. The reaction was then cooled to 0 C. in an ice-water bath and stirred at 0 C. for an additional 10 minutes. Then, a solution of 4-(3-(benzyloxy)-4-chloro-2-methoxyquinoline-6-carbonyl)benzonitrile (335 mg, 0.78 mmol, Intermediate 83: step a) in THF (8 mL) was added. The flask was rinsed with THF (1.5 mL), which was also added to the reaction. The resulting mixture was stirred at 0 C. for 10 minutes, then the ice-water bath was removed and the reaction was allowed to stir at room temperature for 4 hours. The reaction was quenched by the addition of water (15 mL). The aqueous was then extracted with EtOAc (3*20 mL). The organic layers were combined, washed with brine, dried (Na2SO4), filtered and concentrated to dryness. The residue was triturated with Et2O, filtered and dried under air to provide the title compound as a white solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.01-7.99 (m, 1H), 7.80 (d, J=8.7 Hz, 1H), 7.68-7.65 (m, 2H), 7.56-7.53 (m, 3H), 7.53-7.52 (m, 1H), 7.50-7.46 (m, 2H), 7.41-7.34 (m, 3H), 6.45-6.44 (m, 1H), 5.16 (s, 2H), 4.15 (s, 3H), 3.39 (s, 3H). MS (ESI): mass calcd. for C29H23ClN4O3, 510.2. m/z found, 511.0 [M+H]+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methyl-1H-imidazole, its application will become more common.
Reference:
Patent; JOHNSON & JOHNSON; 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.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
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