[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2.[H-].[Na+].[CH3:21]I.[Cl-].[NH4+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:21])[C:6]([C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2
To a solution (10 mL) of 1-(5-chloro-1H-indol-2-yl)heptan-1-one (1.00 g) synthesized in Example A106(2) in N,N-dimethylformamide was added sodium hydride (60%, oily, 182 mg) at 0° C. and the mixture was stirred under argon atmosphere for 30 min. After stirring, methyl iodide (354 μL) was added. The reaction mixture was stirred at room temperature overnight, saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with hexane to give the title object compound (367 mg, 35%) as a pale-brown solid.
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