Ammonium formate → 2-(4-Aminophenyl)-6-hydroxy-3-[3-methoxy-4-(1-pyrrolidinyl)-benzyl]benzo[b]thiophene

Participants

Reaction Steps

2-(4-Aminophenyl)-6-benzyloxy 3-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]benzo[b]thiophene (103 mg) in THF (4.0 mL) was treated with a solution of ammonium formate (25% in H2O, 2.0 mL) and 10% palladium on carbon (100 mg) sequentially at ambient temperature. The resulting mixture was stirred at ambient temperature under argon for 21 h before filtered through diatomaceous earth followed by rinsing with dichloromethane and methanol. The filtrate was extracted with dichloromethane (20 mL×3) from water (30 mL). The combined organic layers were dried with sodium sulfate and concentrated under reduced pressure. Chromatography with Et3N:MeOH:EtOAc (5:10:85) afforded the product (80 mg).

Provenance & Evidence