HCID 53794293, compound → Methyl 2-propylindole-6-carboxylate

HRID 1108679Notes

Reaction equation

HRID 1108679 reaction equation
C(OC([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=2)[CH:13]=[C:12]1[CH2:24][CH2:25][CH3:26])=O)C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[CH2:24]([C:12]1[NH:11][C:19]2[C:14]([CH:13]=1)=[CH:15][CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=2)[CH2:25][CH3:26]

Participants

5

Reactant 1

HCID 53794293HCID 53794293, compound

Product 1

HCID 22627295Methyl 2-propylindole-6-carboxylateYield 90.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 1-benzyloxycarbonyl-2-propylindole-6-carboxylate (200 mg) in a mixture of methanol and ethyl acetate (1:1, 8 ml) was added 10% palladium on carbon (30 mg), and the mixture was stirred under hydrogen atmosphere for 20 minutes. The catalyst was removed by filtration through celite and washed with methanol. The filtrate was evaporated in vacuo to give methyl 2-propylindole-6-carboxylate (112 mg) as colorless crystals.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. washwashed with methanol
  3. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-650c49c65e744fac87910e953180a05d
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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