Potassium Iodide → 2-(6-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione

Participants

Reaction Steps

A suspension of N-hydroxyphthalimide (35.0 g, 214 mmol), 2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (74.8 g, 236 mmol), cesium carbonate (146.8 g, 450 mmol) and potassium iodide (1.78 g, 10.7 mmol) in acetonitrile (350 mL) was stirred at room temperature for 18 h. Water (300 mL) was added, the precipitate was filtered off and washed with water until colourless, then dried in vacuo overnight to yield 2-(6-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione as a colourless solid [85.0 g; 94% of theory; HPLC/MS m/z=400 (M+H); log P(HCOOH)=2.44].

Provenance & Evidence