Synthetic Route of 33468-67-6, These common heterocyclic compound, 33468-67-6, name is 2-Methyl-4-(trifluoromethyl)-1H-imidazole, its 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.
a) To a vial was added 2-methyl-4-(trifluoromethyl)-1H-imidazole (750 mg, 5 mmol), 5 mL of THF, 2.5 mL of DMF, and K2CO3 (2.07 g, 15 mmol). To this mixture was slowly added ethyl bromoacetate (1.00 g, 6 mmol). After 2 hours, the slurry was diluted with EtOAc, filtered on Celite, and concentrated. The residue was purified by flash chromatography (SiO2, 80 g column, eluting with 15-100% EtOAc in hexanes) to provide 476 mg (40%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 7.20 (s, 1H), 4.61 (s, 2H), 4.28 (q, J=7.0 Hz, 2H), 1.63 (s, 3H), 1.31 (t, J=7.0 Hz, 3H); MS: (ES) m/z calculated for C9H12F3N2O2 [M+H]+ 237.1, found 237.1. The regiochemistry of the system was confirmed by nOe between the alpha-methylene and both the imidazole ring and methyl protons.
The synthetic route of 33468-67-6 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ChemoCentryx, Inc.; Chen, Xi; Dragoli, Dean R.; Fan, Pingchen; Li, Yandong; Powers, Jay P.; Punna, Sreenivas; Tanaka, Hiroko; Zhang, Penglie; US2014/57937; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem