Water → Methyl 3-(5-methyl-2-pyridinyl)-5-vinylbenzoate

Participants

Reaction Steps

To a solution of methyl 3-bromo-5-(5-methylpyridin-2-yl)benzoate (2.0 g, 6.53 mmol) in ethanol (13 mL) was added potassium vinyltrifluoroborate (1.31 g 9.80 mmol), triethylamine (1.37 mL, 9.80 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.267 g, 0.327 mmol). The reaction mixture was stirred and microwaved at 140° C. for 10 min. The reaction mixture was cooled to ambient temperature. Water was added, and ethanol was concentrated. The mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate) gave the title compound (1.51 g). MS 254.1 (M+1).

Provenance & Evidence