Sodium Carbonate → tert-Butyl methyl{[5-phenyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methyl}carbamate

Participants

Reaction Conditions

Reaction Steps

A suspension of tert-butyl {[5-bromo-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (1.04 g), phenylboronic acid (0.45 g), tetrakis(triphenylphosphine)palladium (0.42 g) and sodium carbonate (0.77 g) in 1,2-dimethoxyethane (25 mL)-water (25 mL) was stirred at 105° C. for 12 hr. After cooling, saturated aqueous sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate, water and 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=4:1) to give the title compound as a colorless solid (yield 0.97 g, 94%).

Provenance & Evidence