Potassium Carbonate → 2-[3-Fluoro-5-(pyridin-3-yloxy)phenyl]isoindolin-1-one

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Reaction Steps

To a solution of 3-fluoro-5-(pyridine-3-yloxy)aniline (200 mg) in pyridine (5.0 ml), 230 mg of 2-(phenoxymethyl)benzoic acid and 250 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide were added, and the reaction solution was stirred at room temperature for 1 hour. Water and a saturated aqueous ammonium chloride solution were added to the reaction solution, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a 1N aqueous hydrochloric acid solution and a saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude product as colorless oil. To a solution of the obtained crude product in N-methylpyrrolidone (5.0 ml) was added 410 mg of potassium carbonate, and the mixture was stirred at 120° C. for 8 hours. The reaction solution was cooled, thereafter diluted with a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The combined organic layers were washed with water and a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel chromatography to yield the title compound as a white solid.

Provenance & Evidence