3-(1H-Indol-7-yl)-N-methyl-3-phenyl-acrylamide → HCID 59831745, compound

HRID 1716629Notes

Reaction equation

HRID 1716629 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][C:12]([NH:14][CH3:15])=[O:13])[CH:3]=[CH:2]1>CCO.[Pd]>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][C:12]([NH:14][CH3:15])=[O:13])[CH:3]=[CH:2]1

Participants

4

Reactant 1

HCID 691740993-(1H-Indol-7-yl)-N-methyl-3-phenyl-acrylamide

Product 1

HCID 59831745HCID 59831745, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-(1H-indol-7-yl)-N-methyl-3-phenyl-acrylamide XVIII in EtOH (8 ml) was added Degussa's catalyst (10% Pd/C wet, 55 mg). The reaction mixture was subjected to a hydrogenation reaction in a Parr apparatus at 50 psi of H2 for 20 hours. The reaction mixture was filtered through a celite pad, and the filter cake was washed with MeOH. The filtrate was concentrated affording 3-(1H-indol-7-yl)-N-methyl-3-phenyl-propionamide XIX as a white solid in quantitative yield (296 mg).

Workup

  1. customThe reaction mixture was subjected to a hydrogenation reaction in a Parr apparatus at 50 psi of H2 for 20 hours
  2. filtrationThe reaction mixture was filtered through a celite pad
  3. washthe filter cake was washed with MeOH
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8247146e22e342058a653ede35b96ab0
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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