HCID 21196159, compound → HCID 21196116, compound
Reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([O:6][CH2:7][C:8]2[N:9]([CH3:30])[C:10]3[C:15]([C:16]=2[CH2:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][CH:24]([N:27]([CH3:29])[CH3:28])[CH2:23][CH2:22]2)=O)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]2[N:9]([CH3:30])[C:10]3[C:15]([C:16]=2[CH2:17][CH2:18][CH2:19][N:21]2[CH2:26][CH2:25][CH:24]([N:27]([CH3:28])[CH3:29])[CH2:23][CH2:22]2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:31][CH:32]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Under a nitrogen atmosphere around bottom flask is charged with 2-[(4-chlorophenoxy)methyl]-1-methyl-3-[2-[[4-(dimethylamino)piperidin-1-yl]carbonyl]ethyl]-1H-indole (0.194 g, 0.428 mmol). The flask was then placed in an ice bath and boranetetrahydrofuran complex (1.71 ml of a 1.0 M solution in THF, 1.71 mmol) was added. The reaction mixture was then removed from the ice bath and stirred at room temperature for about 90 minutes. The progress of the reaction was monitored by thin layer chromatography. A 1:1 tetrahydrofuran:methanol solution (0.20 ml total) was added, followed by the addition of 2.0 ml of 5.0 N sodium hydroxide.