[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[H-].[Na+].[CH3:13][Si:14]([CH2:17][CH2:18][O:19][CH2:20]Cl)([CH3:16])[CH3:15]>CN(C=O)C.[NH4+].[Cl-]>[Br:1][C:2]1[CH:3]=[C:4]2[CH:5]=[CH:6][N:7]([CH2:20][O:19][CH2:18][CH2:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[C:8]2=[N:9][CH:10]=1To a solution of 5-bromo-7-azaindole (Aldrich, 2 g, 10.15 mmol) in DMF (40.6 ml) at 0° C. was added sodium hydride (0.690 g, 17.26 mmol). The reaction was aged for 10 min followed by addition of SEM-Cl (2.340 ml, 13.20 mmol). The reaction was allowed to warm to RT and stir for 4 h. The mixture was diluted with saturated NH4Cl (30 mL) and product extracted with ethyl acetate (30 mL). The organic extract was washed with brine (30 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (50 g, 0-50% ethyl acetate/hexanes) to give the compound 4-1a (3.2 gm) as a clear oil.
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