Sodium borohydride → HCID 58297378, compound

Participants

Reaction Steps

To an ice cooled solution of (E)-ethyl 3-(1-(4-bromophenyl)-2-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-3-yl)acrylate (400 mg, 0.88 mmol) in 95% ethanol (10 mL) were added BiCl3 (554 mg, 1.76 mmol) and portionwise NaBH4 (134 mg, 3.52 mmol), then the resultant mixture was stirred at room temperature for 12 h. The reaction mixture was filtered, and the filtrate was partitioned between water (50 mL) and ethyl acetate (30 mL), the aqueous layer was extracted with ethyl acetate (30 mL×2). The combined organic layers were washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by preparative TLC (eluting with 50% ethyl acetate in petroleum ether for three times) to give ethyl 3-(1-(4-bromophenyl)-2-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-3-yl)propanoate (5-2) (100 mg, yield: 25%).

Provenance & Evidence