Potassium Carbonate → HCID 66962073, compound

Participants

Reaction Conditions

Reaction Steps

A vinylboronic acid anhydride pyridine complex (86.2 mg (0.36 mmol), 39.3 mg (0.05 mmol) of a [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane complex, and 209.0 mg (1.5 mmol) of potassium carbonate were added to a solution of 241.2 mg (1.0 mmol) of 2,5-dibromopyridine in dioxane-water (4 ml, 3:1), and the mixture was stirred at 80° C. for 3 hr. A saturated aqueous sodium hydrogencarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation to give 208.4 mg of a crude product of 5-bromo-2-vinylpyridine. A 2.0 M dimethylamine methanol solution (5 ml, 10 mmol) was added to a solution of 208.4 mg of the crude product of 5-bromo-2-vinyl pyridine in acetic acid (1.4 ml), and the mixture was stirred at 80° C. overnight and at 90° C. for two nights. A saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was removed by distillation, and the residue was then purified by column chromatography on silica gel (hexane:ethyl acetate=10:1, chloroform:methanol=10:1) to give 49.7 mg (two steps, yield 22%) of the title compound.

Provenance & Evidence