Imidazole → HCID 67176053, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 3-(1-(4-bromophenyl)-2-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-3-yl)propanoate (50 mg, 0.11 mmol), imidazole (68 mg, 10 mmol), L-proline (13 mg, 0.11 mmol), CuI (42 mg, 0.22 mmol), K2CO3 (76 mg, 0.55 mmol) and 4 Å molecular sieve (100 mg) in DMSO (3 mL) was heated at 130° C. for 24 h. 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, and concentrated. The residue was purified by preparative TLC (eluting with 7% methanol in dichloromethane) to give ethyl 3-(1-(4-(1H-imidazol-1-yl)phenyl)-2-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-3-yl)propanoate, (5-3, R1=1H-imidazol-1-yl) (25 mg, yield: 51%), which was used in the next step without further purification.

Provenance & Evidence