[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([OH:20])=[C:15]([CH3:21])[CH:14]=1)=[C:7]2[CH3:22].Br.[CH2:24]([N:26]([CH2:30][CH3:31])[CH2:27][CH2:28]Br)[CH3:25].O>CN(C)C=O>[CH2:24]([N:26]([CH2:30][CH3:31])[CH2:27][CH2:28][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([OH:20])=[C:15]([CH3:21])[CH:14]=1)=[C:7]2[CH3:22])[CH3:25]1.6 g of 60% sodium hydride was suspended in 50 ml of dimethylformamide, and under ice cooling, 5-hydroxy-2-(4-hydroxy-3,5-dimethylphenyl)-3-methylindole was added. After stirring for 30 minutes, 2.8 g of 2-diethylaminoethylbromide hydrobromide was added. The mixture was stirred for 2 hours. The reaction mixture was poured into cold water, and extracted with ethyl acetate. The extract was purified by silica gel column chromatography, and then subjected to thin-layer chromatography to give 5-(2-diethylaminoethoxy)-2-(4-hydroxy-3,5-dimethylphenyl)-3-methylindole.
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