Hydrochloric Acid → HCID 86672052, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of the trifluoroacetic acid salt of 1-[4-chloro-2-(pyridin-2-ylamino)-phenyl]-ethanone (273 mg, 757 μmol) in methanol (3.78 mL) at 25° C. was treated with methyl 4-formylbenzoate (124 mg, 757 μmol) and sodium methoxide in methanol (4.37M, 520 μL, 2.27 mmol). The reaction was stirred at 25° C. for 3 d. At this time, the reaction was diluted with water (50 mL), neutralized with a 1N aqueous hydrochloric acid solution and extracted with methylene chloride (3×50 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to afford 4-{(E)-3-[4-chloro-2-(pyridin-2-ylamino)-phenyl]-3-oxo-propenyl}-benzoic acid methyl ester (287.3 mg, 96.6%) as an orange solid. The material was used without further purification.

Provenance & Evidence