1,2-Dichloroethane → HCID 178426471, compound

Participants

Reaction Steps

3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-methylbenzonitrile (0.046 g, 0.158 mmol), 4-bromo-2-methyl-1H-imidazole-5-carboxylic acid (0.032 g, 0.158 mmol) and DIEA (0.055 mL, 0.316 mmol) were combined in THF (3 mL) and treated with EDC (0.061 g, 0.316 mmol) at 25° C. overnight with stirring. The reaction mixture was concentrated to dryness and partitioned between EtOAc and water. The organic phase was isolated, dried over MgSO4, filtered and concentrated to dryness. The residue was purified on 40 g silica gel eluted with 0 to 10% CH3OH/DCM to give 4-bromo-N-({4-chloro-3-[(3-cyano-5-methylphenyl)oxy]-2-fluorophenyl}methyl)-2-methyl-1H-imidazole-5-carboxamide (0.052 g, 0.109 mmol, 68.8% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6+1 drop D2O) δ ppm 7.38-7.49 (m, 2H), 7.31 (t, J=7.90 Hz, 1H), 7.15 (m, 1H), 7.11 (s, 1H), 4.47 (s, 2H), 2.31 (s, 3H), 2.24 (s, 3 H). LC-MS (ES−) m/z 475.07, 477.03, 479.03 [M−1]. LC-MS (ES+) m/z 477.11, 479.09, 481.07 [M+H].

Provenance & Evidence