Potassium Iodide → HCID 86650762, compound

Participants

Reaction Steps

To a solution of 1-(3,6-dimethylpyrazin-2-yl)-N-hydroxy-1-phenylmethanimine (3.38 g, 14.9 mmol) and 2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (5.19 g, 16.4 mmol) in acetonitrile (50 mL) were added cesium carbonate (10.2 g, 31.2 mmol) and potassium iodide (3.70 mg, 22.3 mmol). After stirring at room temperature for 7 h, the reaction mixture was filtered, the insolubles washed with ethyl acetate, and the combined filtrates concentrated in vacuo, diluted in ethyl acetate (150 mL), washed with water (2×150 mL), dried over MgSO4 and concentrated to dryness in vacuo. Purification on silica gel afforded 2-{6-[({[(3,6-dimethylpyrazin-2-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione [2.79 g, yield 41%; HPLC/MS: m/z=464 (M+H); log P(HCOOH)=3.35].

Provenance & Evidence