Hydrochloric Acid → 3-fluoro-4-[(E)-3-oxo-3-(2-phenylamino-pyridin-3-yl)-propenyl]-benzoic acid methyl ester

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A mixture of 1-(2-phenylamino-pyridin-3-yl)-ethanone (700 mg, 3.3 mmol) in methanol (16.5 mL) at 25° C. was treated with 3-fluoro-4-formyl-benzoic acid methyl ester (601 mg, 3.3 mmol, calculated from 50% mixture) and sodium methoxide in methanol (4.37M, 1.51 mL, 6.6 mmol). The reaction was stirred at 25° C. for 48 h. At this time, the reaction was diluted with water (50 mL), neutralized with a 2N aqueous hydrochloric acid solution, and extracted with methylene chloride (3×75 mL). The combined organics were dried over sodium sulfate and filtered. Silica gel was added to the filtrate, concentrated in vacuo and dried under high vacuum. Flash Chromatography (40 g silica column, 1% methanol/methylene chloride) afforded 3-fluoro-4-[(E)-3-oxo-3-(2-phenylamino-pyridin-3-yl)-propenyl]-benzoic acid methyl ester (1 g, 80.6%) as a red solid.

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