Potassium Carbonate → 8-Methoxy-2-methyl-5-phenylquinoline

Participants

Reaction Conditions

Reaction Steps

5-Bromo-8-methoxy-2-methylquinoline (509 mg) and benzene boronic acid (323 mg) were added to a mixture of 2 M aqueous potassium carbonate (2 ml), toluene (10 ml) and ethanol (1 ml) and refluxed for 30 minutes under a nitrogen atmosphere. The mixture was cooled, triphenylphosphine (75 mg) and dichlorobis(triphenylphosphine)palladium chloride (66 mg) were added and the mixture was heated at 60° C. overnight. After cooling, the reaction mixture was diluted with ethyl acetate (30 ml). The organic phase was washed with 2 M aqueous potassium carbonate solution (2×30 ml), dried (magnesium sulphate), filtered and evaporated in vacuo to give the title compound (272 mg) as an off-white solid.

Provenance & Evidence