COC(C1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Br:14])[CH:12]=2)NC=1)=O.[C:15](=[O:18])([O-])[O-:16].[K+].[K+].[CH3:21][N:22]([CH:24]=O)[CH3:23].I[CH3:27]>ClCCl>[CH3:27][O:16][C:15]([C:13]1[C:8]2[C:21](=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)[N:22]([CH3:23])[CH:24]=1)=[O:18]To a room temperature mixture of 5-bromo-1H-indole-3-carboxylic acid methyl ester (100 mg, 0.394 mmol), potassium carbonate (163 mg, 1.18 mmol) and DMF is added iodomethane (30 μL, 0.47 mmol). After 1.5 hours, additional iodomethane (10 μL) is added and the reaction is stirred for 30 minutes. The reaction mixture is diluted with dichloromethane and filtered. The filtrate is concentrated under high vacuum, diluted with ethyl acetate, and concentrated to give the title compound (105 mg, 99%). ES/MS m/e 270.0 (M+2).
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