1,3-Isobenzofurandione, 5-fluoro- → HCID 17989337, compound

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Reaction Steps

4-Fluorophthalic anhydride [Acros] (0.84 g, 5 mmol) was dissolved in dichloromethane (30 ml) and polymer bound N-cyclohexylcarbodiimide [Argonaut Technologies] (1.69 mol. eq./g, 3 g) was added, followed by a solution of 3-methoxy-4-(2-pyrrolidin-1-yl-ethoxy)-phenylamine [Example A4] (1.18 g, 5.0 mmol) and a catalytic amount of 4-dimethylaminopyridine. The mixture was stirred for 16 h at ambient temperature. The resin was filtered off over filter-aid, and washed with dichloromethane. The filtrate was evaporated in vacuo and purified by chromatography using a Biotage Flash40M cartridge, eluting with dichloromethane-methanol to give the 5-fluoro-2-[3-methoxy-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-isoindole-1,3-dione;

Provenance & Evidence