[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Li]CCCC.[CH3:15][C:16]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])[CH3:17].[Br:23]N1C(=O)CCC1=O>C1COCC1.CCCCCC.N1C=CC=CC=1>[Si:19]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([Br:23])=[CH:2]1)([C:16]([CH3:18])([CH3:17])[CH3:15])([CH3:21])[CH3:20]To a cold (-78°) solution of indole (4.0 g, 34 mmol) in THF (120 mL) was added nBuLi (2.5M/Hexanes) over 5 minutes. The solution was warmed to -10° (ice/salt bath) for 15 minutes, re-cooled to -78° and TBDMS-Cl (5.8 g, 38 mmol) was added in THF (30 mL). The solution was held at 0° for 3 hours, cooled to -78° and N-Bromosuccinimide (6.0 g, 34 mmol) was added in one portion. The solution was stirred coldfor 2 hours and then was allowed to warm to ambient temperature at which time hexane/pyridine (100 mL) was added to the solution and the resulting suspension was filtered over Celite. The organics were evaporated and the residue quickly purified by flash chromatography (hexanes/methylene chloride 2:1) giving 8.5 g of the desired compound as a slightly purple solid.
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