6-iodo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide → N-phenyl-6-vinylimidazo[1,2-a]pyridine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.73 g of 6-iodo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide, 209 mg of tetrakis(triphenylphosphine)palladium(0), 587 μL of tributylvinyltin and 17 mL of DMF is heated for 10 minutes at 130° C. in a microwave machine and then concentrated to dryness. The residue is taken up in 100 mL of water and extracted with twice 70 mL of ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated to dryness under reduced pressure. The solid is triturated in ethyl acetate, filtered off by suction, washed with ethyl acetate and then with isopropyl ether, and taken up in a mixture of methanol and dichloromethane. The insoluble matter is filtered off and washed with methanol. The filtrate is concentrated to dryness under reduced pressure to give 0.29 g of N-phenyl-6-vinylimidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

Provenance & Evidence