[Cl:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.CI.[H-].[Na+].[C:17](O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.CS(C)=O>[Cl:1][C:2]1[N:3]([CH3:17])[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=22-Chloroindole-3-carboxaldehyde (2.69 g) and methyl iodide (4.26 g) were dissolved in a mixed solvent of tetrahydrofuran (25 ml) and dimethylsulfoxide (25 ml), and sodium hydride (0.66 g, 60% mineral oil dispersion) was added thereto at 0° C. A 10% aqueous solution of citric acid was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then a saturated saline, and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was washed with hexane (30 ml) to give 2-chloro-1-methylindole-3-carboxaldehyde (2.54 g).
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