CC(C[AlH]CC(C)C)C.[Br:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[F:20])[N:16]([CH2:21][C:22](OCC)=[O:23])[CH:15]=[CH:14]2.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].CCOCC>C1COCC1>[Br:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[F:20])[N:16]([CH2:21][CH2:22][OH:23])[CH:15]=[CH:14]2
DIBAL-H (1 M in hexanes) (4 mL, 4 mmol) was added to a 0° C. solution of ethyl (5-bromo-6-fluoro-1H-indol-1-yl)acetate (0.480 g, 1.60 mmol) in anhydrous THF (10 mL). The reaction was stirred at rt for 1 h, then treated with saturated aqueous Rochelle's salt and Et2O. The mixture was stirred vigorously for 30 min. The layers were separated and the aqueous layer was further extracted with Et2O. The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated. Chromatography over silica eluting with 60% EtOAc/hexanes afforded the desired compound as an oil.
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