Sodium Carbonate → 4-(5-Methoxy-3-pyridinyl)benzonitrile

Participants

Reaction Steps

1.93 g (10.3 mM) of 3-bromo-5-methoxypyridine and 1.85 g (12.36 mM) of 4-cyanophenylboronic acid are mixed with 40 ml of toluene and 40 ml of methanol. 0.6 g (0.5 mM) of tetrakis(triphenylphosphine)palladium and 1.3 g (30.9 mM) of lithium chloride are added. 26 ml of 1 M sodium carbonate solution are then added. The mixture is refluxed for 5 hours and, after cooling, water and ethyl acetate are added to the reaction medium. The aqueous phase is separated off and extracted with ethyl acetate. The combined organic phases are dried over magnesium sulfate and then concentrated under reduced pressure. The evaporation residue is purified by chromatography on silica gel using a dichloromethane/ethyl acetate mixture (94/6; v/v) as the eluent to give the expected product in the form of a beige solid with a yield of 89%.

Provenance & Evidence