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]A 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 stirred at room temperature. Iodomethane (30 μL, 0.47 mmol) is added. After 1.5 hours, additional iodomethane (10 μL) is added and the reaction is stirred for 30 minutes and diluted with dichloromethane and filtered. The filtrate is concentrated under high vacuum, diluted with ethyl acetate and concentrated to give 105 mg (99%) of the title compound.
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