Bromoacetonitrile → (5-Fluoro-2-oxo-3,4-dihydro-2H-quinoxalin-1-yl)acetonitrile

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Reaction Steps

Sodium hydride (60%, 84 mg, 2.1 mmol) was added to a solution of 5-fluoro-3,4-dihydro-1H-quinoxalin-2-one from Example B (316 mg, 1.9 mmol) in THF (2.0 ml) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 30 mins. Bromoacetonitrile (146 μl, 2.1 mmol) was added and the mixture was stirred for 18 h. Brine was added and the mixture evaporated in vacuo. The residue was portioned between EtOAc and water, separated and the organic phase was dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant 100% pet ether then EtOAc:pet. ether 20:80); yield 183 mg, 47%.

Provenance & Evidence