Related Products 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 flask containing 5-bromo-1-methyl-1H-imidazole (650 mg, 4.04 mmol) was added THF (10 mL) and the clear homogeneous solution was stirred at room temperature as iPrMgCl (2 M in diethylether, 2 mL, 4 mmol) was added. A whitish suspension resulted. The suspension was stirred at room temperature for 30 minutes, then a solution of 4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanone (660 mg, 1.36 mmol, Intermediate 81: step b) in THF (5 mL) containing LaCl3-LiCl complex (0.5 M solution THF, 5 mL, 2.5 mmol) was added to the reaction mixture. The reaction mixture was stirred overnight at 35 C. After 14 hours, the reaction mixture was quenched with saturated aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc (3*40 mL) and the combined organics were washed with brine and dried over MgSO4. The brine portion was back-extracted with DCM (3*40 mL) and dried over MgSO4. The organics were filtered and concentrated to dryness to afford a tan oil. The residue was purified by FCC (2% MeOH-DCM increasing to 10% MeOH) to provide the title compound as an off white solid. 1H NMR (500 MHz, CDCl3) delta 8.13 (d, J=2.0 Hz, 1H), 7.76 (d, J=8.7 Hz, 1H), 7.50 (d, J=8.2 Hz, 2H), 7.44-7.35 (m, 4H), 7.31 (d, J=11.4 Hz, 1H), 7.05 (d, J=8.0 Hz, 1H), 6.90 (d, J=8.0 Hz, 1H), 6.19 (s, 1H), 4.67 (s, 1H), 4.32 (s, 2H), 4.07 (s, 3H), 3.46 (s, 3H), 2.52 (s, 3H), 2.45-2.33 (m, 3H); MS (ESI): mass calcd. Chemical Formula: C30H26ClF3N4O2, Exact Mass: 566.2. m/z found 567.1 [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; 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.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
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