HCID 22627283, compound → HCID 22627407, compound

HRID 1108742Notes

Reaction equation

HRID 1108742 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][CH:34]=[CH:33][C:3]=1[C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17]CC3C=CC=CC=3)=[O:16])[CH:13]=2)[C:8]([C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])=[C:7]1[CH2:30][CH2:31][CH3:32])=[O:5]>CO.[Pd]>[Cl:1][C:2]1[CH:36]=[CH:35][CH:34]=[CH:33][C:3]=1[C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([OH:17])=[O:16])[CH:13]=2)[C:8]([C:25](=[O:29])[CH:26]([CH3:28])[CH3:27])=[C:7]1[CH2:30][CH2:31][CH3:32])=[O:5]

Participants

4

Reactant 1

HCID 22627283HCID 22627283, compound

Product 1

HCID 22627407HCID 22627407, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl 1-(2-chlorobenzoyl)-3-isobutyryl-2-propylindole-6-carboxylate (304 mg) in methanol (6 ml) was hydrogenated over 10% palladium on carbon at 20° C. for 9 hours. The catalyst was filtered off and the filtrate was evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of methanol and chloroform (1:30) to give crystals which were recrystallized From a mixture of ethyl acetate and hexane to give 1-(2-chlorobenzoyl)-3-isobutyryl-2-propylindole-6-carboxylic acid (189 mg) as colorless crystals.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was chromatographed on silica gel eluting with a mixture of methanol and chloroform (1:30)
  4. customto give crystals which
  5. customwere recrystallized From a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-a6b128a07b1543ddbf8fb60cbeaa211e
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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