Water → HCID 15551263, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the crude carbonic acid methyl ester 4-[3-[2-oxo-3-[(1H-pyrrol-2-yl)methylene]-2,3-dihydro-1H-indol-4-yl]-phenylcarbamoyl]-phenyl ester (90 mg, 0.194 mmol) in 2 mL of 1,4-dioxane (Aldrich) was treated with 1.5 mL of distilled water and then powdered potassium hydroxide (25 mg, 0.445 mmol) . The reaction mixture was heated at 90° C. for 1 h. The reaction mixture was then allowed to cool to room temperature and directly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 45% ethyl acetate-hexanes elution) to provide a crude yellow solid containing the desired product and a 1,3-dicyclohexylcarbodiimide derivative. Most of the 1,3-dicyclohexylcarbodiimide derivative was removed by precipitation from an ethanolic solution through the slow addition of distilled water. The precipitated solid was collected by suction filtration. The filtrate was concentrated in vacuo and then directly purified by column chromatography. Two additional rounds of flash chromatography (Merck Silica gel 60, 230-400 mesh, 25% ethyl acetate-hexanes elution each) provided pure (Z)-N-[3-[2,3-dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]-phenyl]-4-hydroxybenzamide (yield: 49 mg, 60%) as a yellow solid (mp 236-238° C.).

Provenance & Evidence