[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=C(C#N)[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:13]([CH3:15])[CH3:14].[OH-:16].[Na+].[CH3:18][CH2:19][OH:20]>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:18]([C:19]([OH:16])=[O:20])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:13]([CH3:15])[CH3:14]To a stirred solution of 5-bromo-3-(1-methylethyl)-1H-indole-7-carbonitrile (1.66 g, 6.31 mmol) in EtOH (45 mL) and water (15 mL) was added 6 N NaOH (10 mL, 60.0 mmol). The reaction was heated at reflux (100° C. oil bath) under N2 for 72 h. LCMS showed that the reaction was complete after 24 h. The reaction was cooled to RT, evaporated to near dryness, diluted with water (˜100 mL), and acidified with 6 N HCl (10 mL). The suspension was triturated, filtered, washed with water and dried under vacuum to give the product 5-bromo-3-(1-methylethyl)-1H-indole-7-carboxylic acid (2.29 g, 8.12 mmol, 129% yield) as an off-white solid. MS (ES)+ m/e 282.4 [M+H]+.
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