[CH:1]([CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=1)=[O:2].[H-].C([Al+]CC(C)C)C(C)C.O>C(Cl)Cl.C1(C)C=CC=CC=1>[OH:2][CH2:1][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=1A solution of 1.0 g of 3-(2-formylethyl)-N-(3-pyridyl)indole in 15 ml of methylene chloride under nitrogen is cooled to -20° and 4.6 ml of 1.75M diisobutylaluminum hydride in toluene is added dropwise. The reaction is allowed to warm to room temperature for 2 hours and 20 ml of water is added with vigorous stirring. The reaction mixture is filtered through celite which is further washed with methylene chloride. The organic phase is separated, dried over potassium carbonate and evaporated to yield 3-(3-hydroxypropyl)-N-(3-pyridyl)indole as an oil; IR (CH2Cl2) 3480 cm-1.
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