[H-].[Li+].[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[F:14])[NH:10][C:9](=[O:15])[CH:8]=[N:7]2.Br[CH2:17][CH2:18][CH:19]1[O:23][CH2:22][CH2:21][O:20]1.O>CN(C)C=O>[O:20]1[CH2:21][CH2:22][O:23][CH:19]1[CH2:18][CH2:17][N:10]1[C:11]2[C:6](=[CH:5][C:4]([F:3])=[C:13]([F:14])[CH:12]=2)[N:7]=[CH:8][C:9]1=[O:15]Lithium hydride (52 mg, 6.5 mmol) was added to a solution of 6,7-difluoroquinoxalin-2(1H)one (1 g, 5.4 mmol) in N,N-dimethylformamide (10 ml) under cooling on ice and the reaction mixture was stirred at room temperature for 30 minutes. The mixture was cooled on ice again, a solution of 2-(2-bromoethyl)-1,3-dioxolane (0.8 ml, 6.5 mmol) in N,N-dimethylformamide (2 ml) was gradually added thereto and the obtained mixture was stirred for 4 hours. Water was gradually added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 0.6 g (39%) of the title compound.
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