Water → Ethyl 4-(hydroxymethyl)-2-methylpyrazolo[1,5-a]pyridine-3-carboxylate

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Reaction Steps

To a solution of 1-amino-3-(hydroxymethyl)pyridinium 2,4-dinitrobenzenolate (200 g, 0.650 mol) in dimethylformamide (1.3 L) was added potassium carbonate (224 g, 1.62 mol). To the mixture was added ethyl 2-butynoate (72.8 g, 0.650 mol) at room temperature, and the mixture was stirred for 12 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/3) to give the title compound (41.0 g, yield 27%).

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