Acetic Anhydride → HCID 15870844, compound

Participants

Reaction Steps

In 2 ml of methylene chloride was dissolved 200 mg of ethyl 2,5-difluoro-3-methyl-4-[2-(p-toluenesulfonyl)isoindolin-5-yl]benzoylacetate, and to this solution were added 76 mg of acetic anhydride and 90 mg of N,N-dimethylformamide dimethyl acetal, after which the resulting mixture was stirred at room temperature for two hours. Thereafter, the solvent was removed by distillation under reduced pressure. The residue obtained was dissolved in 1 ml of ethanol, and a solution of 58 mg of 2-fluoroethylamine hydrochloride and 27 mg of sodium methoxide in 1 ml of ethanol was added to the solution, after which the resulting mixture was stirred at room temperature for 20 minutes. The reaction mixture was concentrated under reduced pressure, and the residue obtained was dissolved in 2 ml of N,N-dimethylformamide, after which 65 mg of potassium carbonate was added to the solution. The resulting mixture was stirred at 100° C. for one hour. The reaction mixture was cooled to room temperature, and thereafter, water was added to the mixture. The resulting precipitate was collected by filtration, and the pale yellow solid obtained was purified by a column chromatography (eluent: n-hexane:ethyl acetate=2:1). And diisopropyl ether was thereafter added thereto, after which the crystals formed were collected by filtration, to obtain 126 mg of colorless, crystalline ethyl 6-fluoro-1-(2-fluoroethyl)-8-methyl-7-[2-(p-toluenesulfonyl)isoindolin-5-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylate.

Provenance & Evidence