(Prop-2-en-1-yl)stannane → 5-Allyl-4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-iodo-benzoic acid methyl ester (2.39 g in 12 mL N,N-dimethylformamide) and 0.183 g bis(triphenylphosphine)palladium(II) chloride was added 2.02 mL allyltin and the mixture heated to 100° C. on an oil bath. After 2 hours, the mixture was cooled, partitioned between ethyl acetate and water and the organic layer washed further with brine. Concentration of the dried (magnesium sulfate) organics and purification by flash chromatography on silica gel (hexane:ethyl acetate, 95:5; then 90:10) gave the title compound (1.4 g).

Provenance & Evidence