Imidazole → HCID 67175664, compound

Participants

Reaction Steps

To a mixture of 3-(3-(4-bromophenyl)-2-(4-cyano-2-methylphenyl)-1H-pyrrol-1-yl)propanoic acid (400 mg, 0.98 mmol) and imidazole (200 mg, 2.94 mol) in DMSO (5 mL) was added L-proline (33.8 mg, 0.294 mmol), CuI (111.7 mg, 0.588 mmol) and K2CO3 (270 mg, 1.96 mmol), then the resultant mixture was stirred at 100° C. overnight. After being cooled down to room temperature, the reaction mixture was filtered, and the filter cake was washed with ethyl acetate (10 mL×3). The combined filtrate was washed with saturated NaHCO3 aqueous solution (30 mL), and the aqueous layer was extracted with ethyl acetate (15 mL×3). The combined organic layers were washed with brine, dried over MgSO4, concentrated. The residue was purified by silica gel column (DCM: MeOH=30:1-20:1) to afford 3-(3-(4-(1H-imidazol-1-yl)phenyl)-2-(4-cyano-2-methylphenyl)-1H-pyrrol-1-yl)propanoic acid (190 mg, yield 48.9%) as a solid.

Provenance & Evidence