Potassium Carbonate → N-(3-bromo-2-methylphenyl)-1-(2,2-diethoxyethyl)-1H-imidazole-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

Step 2 A solution of N-(3-bromo-2-methylphenyl)-1H-imidazole-2-carboxamide (0.70 g, 2.499 mmol) in DMF (12.5 mL) was treated with potassium carbonate (0.794 g, 5.75 mmol) and 2-bromo-1,1-diethoxyethane (0.395 mL, 2.62 mmol). The suspension was heated at 100° C. overnight. The mixture was cooled to rt, diluted with water and extracted with EtOAc. The organic phase was washed with brine, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 85:15 to 20:80 hexane-EtOAc) to provide N-(3-bromo-2-methylphenyl)-1-(2,2-diethoxyethyl)-1H-imidazole-2-carboxamide as a white solid (0.81 g, 82%). 1H NMR (400 MHz, DMSO-d6) δ 10.17 (1H, s), 7.51 (1H, d, J=2.6 Hz), 7.49 (1H, d, J=2.6 Hz), 7.44 (1H, d, J=1.1 Hz), 7.18 (1H, t, J=8.0 Hz), 7.10 (1H, d, J=1.1 Hz), 4.75 (1H, t, J=5.4 Hz), 4.52 (2H, d, J=5.3 Hz), 3.63 (2H, dq, J=9.7, 7.0 Hz), 3.35-3.44 (2H, m), 2.31 (3H, s), 1.05 (6H, t, J=7.0 Hz). Mass spectrum m/z 396, 398 (M+H)+.

Provenance & Evidence