Sodium Iodide → 1-[2-(tert-Butyldimethylsilanyloxy)ethyl]-5-fluoro-3,4-dihydro-1H-quinoxalin-2-one

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Reaction Steps

Sodium hydride (60%, 128 mg, 3.2 mmol) was added to a solution of 5-fluoro-3,4-dihydro-1H-quinoxalin-2-one from Example B (530 mg, 3.2 mmol) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 10 min. (2-Bromoethoxy)-tert-butyldimethylsilane (789 mg, 3.3 mmol) and sodium iodide (495 mg, 3.3 mmol) were added and the mixture was stirred for 18 h. Brine was added and the mixture was evaporated in vacuo. The residue was taken up in EtOAc and brine, separated and the organic layer was dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc:pet.ether 40:60) to give a pale yellow solid: yield 600 mg, 58%.

Provenance & Evidence