4-(3-Methoxy-1-propinyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone → HCID 68492207, compound

HRID 21225Notes

Reaction equation

HRID 21225 reaction equation
[CH3:1][O:2][CH2:3][C:4]#[C:5][C:6]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:17]3[C:22]([CH:23]=2)=[CH:21][C:20]([CH2:24][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:19][CH:18]=3)=[C:11]2[C:7]=1[CH2:8][NH:9][C:10]2=[O:38].[H][H]>CO.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[C:17]3[C:22]([CH:23]=2)=[CH:21][C:20]([CH2:24][N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)=[CH:19][CH:18]=3)=[C:11]2[C:7]=1[CH2:8][NH:9][C:10]2=[O:38]

Participants

5

Reactant 2

HCID 1317282364-(3-Methoxy-1-propinyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinoneHCID 178418361HCID 178418361, compound

Product 1

HCID 68492207HCID 68492207, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a similar manner to Step 1 of Example 328, 4-(3-methoxy-1-propinyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (157 mg, 0.306 mmol) was dissolved in methanol (6.3 mL), and the solution was added with 10% Pd—C (46 mg) to react hydrogen. The reaction mixture was filtered using Celite. The solvent of the filtrate was evaporated under reduced pressure to obtain 4-(3-methoxypropyl)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (152 mg, yield 96%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customThe solvent of the filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cfb4a1b5fecc4702a1c503e75f5509fa
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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