Dichloromethane → HCID 90460781, compound

Participants

Reaction Steps

A mixture of ethyl 4-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-imidazole-5-carboxylate (3.48 g, 9.96 mmol, 1.00 equiv), (4-cyanophenyl)boronic acid (3.0 g, 20.42 mmol, 2.00 equiv), Pd(dppf)Cl2.CH2Cl2 (0.42 g, 0.06 equiv) and potassium carbonate (4.0 g, 3.00 equiv) in N,N-dimethylformamide (20 mL) was stirred under nitrogen at 100° C. for 5 h. The reaction was cooled to room temperature and then diluted with 100 mL of ethyl acetate. The mixture was washed with 4×50 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified on a silica gel column eluted with 0-20% of ethyl acetate in petroleum ether to give 3.05 g (82%) of ethyl 4-(4-cyanophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-5-carboxylate as a yellow oil. LCMS (method A, ESI): RT=1.62 min, m/z=372.0 [M+H]+.

Provenance & Evidence