Potassium Iodide → 2-{6-[({[(1-methyl-1H-imidazol-5-yl)(2-thienyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione

Participants

Reaction Steps

To a solution of N-hydroxy-1-(1-methyl-1H-imidazol-5-yl)-1-(2-thienyl)methanimine (4.10 g, 19.8 mmol) and 2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (6.89 g, 21.7 mmol) in acetonitrile (100 mL) were added cesium carbonate (13.5 g, 41.4 mmol) and potassium iodide (328 mg, 1.98 mmol). After stirring at room temperature for 24 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)(2-thienyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione [7.91 g, yield 86%; HPLC/MS: m/z=444 (M+H); log P(HCOOH)=1.66].

Provenance & Evidence