[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:7][CH:8]=2)C=[CH:2]1.P(Cl)(Cl)(Cl)=O.[OH-:24].[K+].Cl.Cl[CH2:28][CH2:29]Cl>CN(C)C=O>[O:16]1[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][O:10][C:6]2[CH:7]=[C:8]3[C:9](=[CH:4][CH:5]=2)[NH:1][CH:2]=[C:28]3[CH:29]=[O:24])[CH2:14][CH2:15]1Under an argon atmosphere, a solution of 4-[2-(1H-indol-5-yloxy)ethyl]morpholine (0.12 g, 0.5 mmol) in 1,2-dichloroethane (2.0 mL) was added dropwise with a solution of phosphorus oxychloride (0.1 mL) and N,N-dimethylformamide (0.1 mL) in 1,2-dichloroethane (1.0 mL). The mixture was stirred at room temperature for 1 hour, and then added with 3 N aqueous potassium hydroxide, and the mixture was stirred at 60° C. for 2 hours. The aqueous layer was adjusted to pH 7 with 3 N hydrochloric acid, and then extracted with ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was suspended in a mixed solvent of ethyl acetate and hexane and thereby washed to obtain 5-(2-morpholinoethoxy)-1H-indole-3-carboxaldehyde (0.068 g, 50%).
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