Potassium Carbonate → HCID 90460509, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 1H-imidazole-4-carboxylate (10 g, 71.36 mmol, 1.00 equiv), CuI (2.7 g, 14.18 mmol, 0.20 equiv), potassium carbonate (30 g, 217.06 mmol, 3.02 equiv), 4-iodobenzonitrile (25 g, 109.16 mmol, 1.53 equiv) and (1S,2S)-1-N,2-N-dimethylcyclohexane-1,2-diamine (2.0 g, 14.06 mmol, 0.20 equiv) in 1,4-dioxane (200 mL) was stirred under nitrogen at 95° C. overnight. The reaction was cooled to room temperature and the solid material was removed by filtration. The filtrate was diluted with 800 mL of ethyl acetate then washed with 3×400 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 1-3% of methanol in dichloromethane to give 450 mg (3%) of ethyl 1-(4-cyanophenyl)-1H-imidazole-5-carboxylate as a white solid. 1H-NMR (300 MHz, DMSO-d6): δ 8.19 (d, J=0.9 Hz, 2H), 7.84 (d, J=0.9 Hz, 2H), 4.15 (q, J=5.4 Hz, 2H), 1.16 (t, J=5.1 Hz, 3H) ppm. LCMS (method D, ESI): RT=1.19 min, m/z=242.0 [M+H]+ and 1.2 g (7%) of ethyl 1-(4-cyanophenyl)-1H-imidazole-4-carboxylate as a white solid. 1H-NMR (300 MHz, CDCl3): δ 7.90 (s, 1H), 7.82-7.76 (m, 3H), 7.50-7.47 (m, 2H), 4.24 (q, J=7.2 Hz, 2H), 1.28 (t, J=7.2 Hz, 3H) ppm. LCMS (method D, ESI): RT=1.16 min, m/z=242.0 [M+H]+.

Provenance & Evidence