[H-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:10]2)=[CH:6][CH:5]=1.IC.[CH2:20](O)C>CN(C)C=O>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:10]2[CH3:20])=[CH:6][CH:5]=1A suspension of 1.8 g (45 mmol) of 60% sodium hydride (washed beforehand with petroleum ether) and of 8.0 g (35.8 mmol) of ethyl 6-chloro-1H-indole-2-carboxylate in 80 ml of N,N-dimethylformamide is stirred for 2 h at room temperature, 2.8 ml (45 mmol) of iodomethane are subsequently added and the mixture is stirred at room temperature for 4 h. 5 ml of absolute ethanol are added and the solvent is evaporated under reduced pressure. The residue is taken up in water and the mixture is extracted with dichloromethane, the organic phase is dried and filtered, the solvent is evaporated under reduced pressure and the residue is purified by chromatography on a column of silica gel. 8.5 g (35.7 mmol) of a white crystalline compound are isolated.
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