Potassium Iodide → HCID 86650758, compound

Participants

Reaction Steps

To a solution of N-hydroxy-1-(1-methyl-1H-imidazol-5-yl)-1-(3-thienyl)methanimine (4.96 g, 23.9 mmol) and 2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (8.35 g, 26.3 mmol) in acetonitrile (100 mL) were added cesium carbonate (16.4 g, 50.3 mmol) and potassium iodide (397 mg, 2.39 mmol). After stirring at room temperature for 28 h, the reaction mixture was filtered, the insolubles washed with ethyl acetate, and the combined filtrates concentrated in vacuo. Purification on silica gel afforded 2-{6-[({[(1-methyl-1H-imidazol-5-yl)(3-thienyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione [6.91 g, yield 62%; HPLC/MS: m/z=444 (M+H); log P(HCOOH)=1.73].

Provenance & Evidence