[H-].[Na+].C([CH:5]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)[C:6]([OH:8])=[O:7])C.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:26](OCC)(=O)[CH3:27].CCCCCC>CN(C)C=O>[CH2:18]([N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9]([CH2:5][C:6]([O:8][CH2:26][CH3:27])=[O:7])=[CH:10]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1Combine sodium hydride (1.08 g, 60% in oil, 27.1 mmol) and dimethylformamide (50 mL). Add a solution of ethyl indol-3-yl-acetic acid (5 g, 24.6 mmol) in dimethylformamide (20 mL). Stir until gas evolution ceases. Add benzyl bromide (5.85 mL, 49.2 mmol). Warm to ambient temperature. After 48 hours, partition the reaction mixture between ethyl acetate and water. Separate the organic layer and extract with a saturated sodium chloride solution. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 10% ethyl acetate/hexane to give the title compound.
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