2-Bromo-6-methylpyridine → 2-(5-Benzo[1,3]dioxol-5-yl-oxazol4-yl)-6-methyl-pyridine

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Reaction Steps

A solution of 5-benzo[1,3]dioxol-5-yl-4-bromo-oxazole (156 mg, 0.58 mmol), 2-bromo-6-methyl-pyridine (100 mg, 0.58 mmol, 1 equiv), 1,1,1,2,2,2-hexamethyl-distannane (190 mg, 0.58 mmol, 1 equiv) and tetrakis(triphenylphosphine)palladium(0) (67 mg, 0.058 mmol, 0.1 equiv) in 1,4-dioxane (6 mL) was heated to reflux overnight. The resulting reaction mixture was cooled to ambient temperature and concentrated in vacuo. Silica gel chromatography (gradient from hexane to 30% ethyl acetate in hexane) provided 2-(5-Benzo[1,3]dioxol-5-yl-oxazol4-yl)-6-methyl-pyridine (114 mg, 70%).[LCMS: Rt=1.79 min, M+H=281.2]

Provenance & Evidence