Dimethylformamide → HCID 67396667, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl {[1-[(4-bromo-3-thienyl)sulfonyl]-4-fluoro-5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl]methyl}methylcarbamate (229 mg) in dimethylformamide (3 mL) was added zinc cyanide (74.6 mg) at room temperature, and the mixture was sufficiently deaerated under an argon atmosphere. Tetrakis(triphenylphosphine)palladium (0) (145 mg) was added and the mixture was further deaerated and stirred at 120° C. for 2 hr. The reaction mixture was diluted with ethyl acetate and filtrated. The filtrate was washed with water, and separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→3:2) to give the title compound as a pale-yellow oil (yield 181 mg, 88%).

Provenance & Evidence