Potassium Carbonate → 3-Chloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-2-ethenylpyridine

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Reaction Steps

In a sealed tube charged with a solution of 2,3-dichloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)pyridine (1500 mg, 5.13 mmol) in 1,4-dioxane (20 ml) was added K2CO3 (2128 mg, 15.40 mmol). The mixture was degassed with N2, then vinylboronic anhydride pyridine complex (1235 mg, 5.13 mmol) and tetrakis(triphenylphosphine)palladium (0) (178 mg, 0.154 mmol) were added. The reaction mixture was stirred at reflux temperature overnight. The crude was diluted with water and extracted twice with EtOAc. The combined organic phases were washed with water and with sat. NaCl, dried over anhydrous MgSO4 and concentrated under vacuum. Purification by flash chromatography using Flashmaster II, a 50 g Merck silica gel cartridge, and mixtures of hexane and EtOAc as eluent afforded 3-chloro-5-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-2-ethenylpyridine (754 mg, 49%).

Provenance & Evidence