Tributylvinyltin → {1-[4-(4-oxo-2-phenyl-8-vinyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of {1-[4-(8-bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (100 mg, 0.183 mmol) in anhydrous toluene (3 mL) was degassed using argon. Tetrakis(triphenylphosphine)palladium(0) (21 mg, 0.018 mmol) and tributyl(vinyl)tin (0.080 mL, 0.274 mmol) were added. The reaction vial was degassed using argon and the reaction mixture was stirred at 90° C. for 2 h. The resultant mixture was allowed to cool to RT and subjected to flash chromatography (SiO2, gradient 0 to 40% EtOAc in cyclohexane) to give the title compound as a gummy solid (81 mg, 90%). LCMS (Method G): RT=4.73 min, [M+H]+=494.

Provenance & Evidence