Sodium Iodide → 1-(3-Aminopropyl)-5-fluoro-3,4-dihydro-1H-quinoxalin-2-one

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Reaction Steps

Sodium hydride (60%, 48 mg, 1.2 mmol) was added to a solution of 5-fluoro-3,4-dihydro-1H-quinoxalin-2-one from Example B (200 mg, 1.2 mmol) in DMF (3 ml) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 10 mins. (3-Bromopropyl)carbamic acid tert-butyl ester (290 mg, 1.2 mmol) and sodium iodide (180 mg, 1.2 mmol) were added and the mixture was stirred at room temperature for 18 h. Brine was added and the mixture was evaporated in vacuo. The residue was partitioned between EtOAc and brine, separated and the organic phase was dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc:pet. ether 50:50) to give a pale yellow gum; yield 230 mg, 59%.

Provenance & Evidence