[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[NH:4][CH2:5][C:6](=[O:12])[NH:7]2.[H-].[Na+].Br[CH2:16][C:17]([O:19][CH3:20])=[O:18]>CN(C=O)C.[Cl-].[Na+].O>[CH3:20][O:19][C:17](=[O:18])[CH2:16][N:7]1[C:8]2[C:3](=[C:2]([F:1])[CH:11]=[CH:10][CH:9]=2)[NH:4][CH2:5][C:6]1=[O:12]To a solution of 5-fluoro-3,4-dihydro-1H-quinoxalin-2-one from Example B (150 mg, 0.90 mmol) in DMF (3.0 ml) was added sodium hydride (60%, 36 mg, 0.90 mmol) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 0.5 h. The mixture was cooled again in an ice/water bath and methyl bromoacetate (85 μl, 0.90 mmol) was added. The mixture was allowed to warm slowly to room temperature and stirred for 18 h. Brine was added and the mixture was evaporated in vacuo. The residue was partitioned between EtOAc and brine and separated. The organic phase was dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc:pet ether 40:60) to give a white solid; yield 140 mg, 65%.
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