Methyl[6-chloro-2-(3-benzyloxybenzoyl)-1h-indol-3-yl]acetate → Methyl[6-chloro-2-(3-hydroxybenzoyl)-1h-indol-3-yl]acetate

HRID 396514Notes

Reaction equation

HRID 396514 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:30])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22]CC2C=CC=CC=2)[CH:17]=1>C(OCC)(=O)C.CO.[Pd]>[CH3:1][O:2][C:3](=[O:31])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15](=[O:30])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=1

Participants

4

Reactant 1

HCID 23003368Methyl[6-chloro-2-(3-benzyloxybenzoyl)-1h-indol-3-yl]acetate

Product 1

HCID 23003551Methyl[6-chloro-2-(3-hydroxybenzoyl)-1h-indol-3-yl]acetateYield 24%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of methyl[6-chloro-2-(3-benzyloxybenzoyl)-1H-indol-3-yl]acetate (Example 177, 0.37 g, 0.85 mmol) and 10% palladium-charcoal (80 mg) in ethyl acetate-methanol (5:1, 30 ml) was stirred under hydrogen atmosphere for 2.5 h. The mixture was filtered thorough a pad of Celite and the filtrate was concentrated. The solids were washed with dichloromethane (10 ml) to afford 70mg (24%) of the title compound as white solids.

Workup

  1. filtrationThe mixture was filtered thorough a pad of Celite
  2. concentrationthe filtrate was concentrated
  3. washThe solids were washed with dichloromethane (10 ml)

Sources & evidence

ORD record
ord-d17d77736b85464a97e6175013eb4868
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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