HCID 22627283, compound → HCID 22627407, compound

HRID 278127Notes

Reaction equation

HRID 278127 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-bf8f3f424ef04f0c83644697226519c6
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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