[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18](OCC)=[O:19])=[CH:12]2)#[N:8].CO>C1COCC1>[OH:19][CH2:18][C:13]1[NH:14][C:15]2[C:11]([CH:12]=1)=[CH:10][C:9]([C:7]#[N:8])=[CH:17][CH:16]=2LiAlH4 (1.0 M in THF, 5 mL) was added to a solution of ethyl 5-cyano-1H-indole-2-carboxylate (D21) (1 g) in THF (100 mL). The reaction mixture was stirred for 15 min at RT. MeOH was added to quench the reaction. The solvent was evaporated. EtOAc (500 mL) was added. The organic solution was washed with aqueous HCl (300 mL), then was dried over anhydrous magnesium sulfate. The dried solution was concentrated to afford 2-(hydroxymethyl)-1H-indole-5-carbonitrile (D24) (600 mg) as a pale orange oil. MS (ES): C10H8N2O requires 172; found 173.2 (M+H+)
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