Acetic Acid → 1-(6-Methylpyridin-2-YL)-2-(quinolin-6-YL)ethanone

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-chloro-quinoline (2.08 g, 12.3 mmol) in tetrahydrofuran (50 mL) was added 1-(6-methyl-pyridin-2-yl)-ethanone of Step B (2.0 g, 14.8 mmol, 1.1 equiv), palladium acetate (0.055 g, 0.25 mmol, 0.02 equiv), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (0.197 g, 0.50 mmol, 0.04 equiv), and potassium tert-butoxide (3.76 g, 30.75 mmol, 2.2 equiv). The resulting reaction mixture was heated to 80° C. for 18 hours, then cooled down to 20° C., and slowly treated with acetic acid (3 mL). The resulting solids were filtered off, and the mother liquor was concentrated in vacuo. Silica gel chromatography (3:1 hexane/acetone) yielded the title compound (2.52 g, 78%).

Provenance & Evidence