4-(3-Hydroxy-1-propynyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone → 4-(3-Hydroxypropyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone
Reaction equation
[OH:1][CH2:2][C:3]#[C:4][C:5]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:16]3[C:21]([CH:22]=2)=[CH:20][C:19]([CH2:23][N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[CH:18][CH:17]=3)=[C:10]2[C:6]=1[CH2:7][NH:8][C:9]2=[O:37]>CO.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]([C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[C:16]3[C:21]([CH:22]=2)=[CH:20][C:19]([CH2:23][N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[CH:18][CH:17]=3)=[C:10]2[C:6]=1[CH2:7][NH:8][C:9]2=[O:37]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
4-(3-Hydroxy-1-propynyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (89.7 mg, 0.180 mmol) was dissolved in methanol (5.4 mL), and the solution was added with 10% Pd—C (16.8 mg), followed by stirring at room temperature for 2.7 hours under hydrogen atmosphere at normal pressure. The mixture was added with 10% Pd—C (8.9 mg), and further stirred for 2.5 hours. The reaction mixture was filtered using Celite. The solvent of filtrate was evaporated under reduced pressure to obtain 4-(3-hydroxypropyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (84.6 mg, yield 93%).
Workup
- stirringfurther stirred for 2.5 hours
- filtrationThe reaction mixture was filtered
- customThe solvent of filtrate was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-d51687e5ee77423cb34324c432e99971
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745641B2
Reaction notes
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