Ethane, 2-bromo-1,1-diethoxy- → Methyl imidazo(1,2-a)pyridine-6-carboxylate

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Reaction Steps

A solution of bromoacetaldehyde diethyl acetal (3.2 mL, 21.3 mmol) in 12M HCl (0.5 mL) and water (23 mL) was heated at 90° C. for 1 hour, cooled to room temperature, treated sequentially with NaHCO3, (1.67 g, 20 mmol) and methyl 6-aminonicotinate (1.10 g, 7.0 mmol), heated at 60° C. for 30 minutes, cooled to room temperature, adjusted to pH 9, and extracted with ethyl acetate. The extract was washed with water, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography with 97.5:2.5 dichloromethane/methanol to provide 1.02 g (88%) of the desired product.

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