Water → 5-Bromo-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl ester

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Reaction Steps

A solution of 5-bromo-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid (2.48 g, 9 mmol), iodomethane (2.55 g, 18 mmol) and sodium carbonate (0.106 g, 9 mmol) in DMF (30 mL) was stirred overnight at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed three times with brine, dried (sodium sulfate) and evaporated. The residue was purified by column chromatography (silica gel, 50 g, 30% ethyl acetate in petroleum ether) to yield the title compound (1.7 g, 6 mmol, 65%) as yellow solid; MS (EI): m/e 290.0 [M+H]+.

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