Sodium hydride → 1-{2-[(6-Bromopyridin-3-yl)oxy]ethyl}pyrrolidine-2,5-dione

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Reaction Steps

10 g (58 mmol) of 3-hydroxy-6-bromopyridine were dissolved in 40 ml of DMF and treated with 2.76 g (69 mmol) of sodium hydride (60% suspension in mineral oil). After stirring at room temperature for 1 h, 20 mg of 4-dimethylaminopyridine were added and the mixture was treated with 16.53 g (74.8 mmol) of methanesulfonic acid 2-(2,5-dioxopyrrolidin-1-yl)ethyl ester and heated to 100° C. for 3 h. Subsequently, the solvent was evaporated and the residue was taken up in water and extracted 4 times with ethyl acetate. The combined organic phases were dried and evaporated to dryness. The remaining material was purified by chromatography (silica gel, dichloromethane/methanol 98:2) followed by preparative HPLC (RP18, acetonitrile/water containing 0.1% TFA) to yield 10.8 g of the title compound.

Provenance & Evidence