Sodium Carbonate → Benzyl[3-(aminocarbonyl)-5-(2,4-difluorophenyl)-2-thienyl]carbamate

Participants

Reaction Conditions

Reaction Steps

A suspension of benzyl[3-(aminocarbonyl)-5-iodo-2-thienyl]carbamate (250 mg, 0.622 mmol), 2,4-difluorophenylboronic acid (349 mg, 2.21 mmol), dichlorobis(triphenylphosphine)palladium (21.8 mg, 0.031 mmol), and sodium carbonate (6.22 mL, 12.43 mmol) in 1,2-dimethoxyethane (10 mL) sealed in a 5 mL microwave reaction vessel was purged of oxygen by doing 5 vacuum/argon flush cycles. The reaction solution was heated in a Biotage microwave for five minutes at 100° C. The resulting mixture was partitioned between ethyl acetate (30 mL) and saturated aqueous sodium bicarbonate (20 mL). The layers were separated and the organic layer was washed with saturated sodium bicarbonate (20 mL) and brine (2×20 mL), dried over sodium sulfate, filtered, and concentrated. The crude material was purified by silica gel chromatography using a 0-4% methanol/dichloromethane elution to afford the title compound.

Provenance & Evidence