HCID 69589439, compound → HCID 12149362, compound

HRID 351646Notes

Reaction equation

HRID 351646 reaction equation
[CH2:1]([O:5][C:6]1[CH:28]=[CH:27][C:9]([C:10]([N:12]2[C:20]3[C:15](=[C:16]([CH:21]=[CH:22][C:23]([OH:25])=[O:24])[CH:17]=[CH:18][CH:19]=3)[CH:14]=[C:13]2[CH3:26])=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[H][H]>CO.C(OCC)(=O)C.[Pd]>[CH2:1]([O:5][C:6]1[CH:28]=[CH:27][C:9]([C:10]([N:12]2[C:20]3[C:15](=[C:16]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH:17]=[CH:18][CH:19]=3)[CH:14]=[C:13]2[CH3:26])=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 69589439HCID 69589439, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12149362HCID 12149362, compoundYield 8.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 3-(1-(4-butoxybenzoyl)-2-methylindol-4-yl)acrylic acid (300 mg; prepared in Example 4) in methanol—ethyl acetate (5 ml+5 ml) was added palladium on activated carbon (100 mg) at room temperature. The inside of the vessel was replaced with hydrogen and the mixture was stirred at room temperature for 2 hours. The mixture was filtered through Celite (trademark). The filtrate and washing with chloroform were combined, and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform—methanol) to give the title compound (25 mg) having the following physical data.

Workup

  1. filtrationThe mixture was filtered through Celite (trademark)
  2. washThe filtrate and washing with chloroform
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (chloroform—methanol)

Sources & evidence

ORD record
ord-5f77098e3f544115ba1ac2cb17921d32
Source dataset
uspto-grants-2004_06
Patent number
US06743793B2

Reaction notes

Loading…