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To a solution of 2-phenyl-1H-indole (0.94 g, 4.85 mmol) in N,N-dimethylformamide (10 mL) was added sodium hydride (60% in oil, 0.19 g, 4.85 mmol) with stirring at 0° C., and the mixture was stirred at the same temperature for 5 min. 3-(Chloromethyl)-4-isobutoxybenzaldehyde (1.0 g, 4.41 mmol) and sodium iodide (0.73 g, 4.85 mmol) were added to the obtained mixture and the mixture was stirred at the same temperature for 2 hr. After completion of the reaction, the reaction mixture was diluted with ethyl acetate, and the mixture was washed with 5% aqueous potassium hydrogensulfate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=4/1) to give the title compound (0.60 g, yield 36%) as colorless crystals.

1. stirringthe mixture was stirred at the same temperature for 5 min
2. stirringthe mixture was stirred at the same temperature for 2 hr
3. customAfter completion of the reaction
4. washthe mixture was washed with 5% aqueous potassium hydrogensulfate solution and saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=4/1)