[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].O>CN(C=O)C>[Si:13]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([F:3])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]At 0° C., NaH (1.88 g, 46.2 mmol) was added to a solution of 5-fluoro-1H-indole (5.2 g, 38.5 mmol) in 40 mL DMF. After 10 min at 0° C. tert-butyldimethylsilyl chloride (6.96 g, 46.2 mmol) was added and the mixture allowed to stir at 0° C. for an additional 1 h. The mixture was warmed to room temperature and stirred overnight, then diluted by the addition of water and extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated and purified by silica gel column chromatography to give the title compound (6.5 g, 67.7%)
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