N-Methyl-3-(2-methyl-1H-indol-5-yl)-3-phenyl-acrylamide → N-methyl-3-(2-methyl-1H-indol-5-yl)-3-phenyl-propionamide

HRID 268802Notes

Reaction equation

HRID 268802 reaction equation
[CH3:1][NH:2][C:3](=[O:22])[CH:4]=[C:5]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([CH3:21])=[CH:15]2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CCO.CCOC(C)=O.CO.[Pd]>[CH3:1][NH:2][C:3](=[O:22])[CH2:4][CH:5]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([CH3:21])=[CH:15]2)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 67356049N-Methyl-3-(2-methyl-1H-indol-5-yl)-3-phenyl-acrylamide

Product 1

HCID 59831697N-methyl-3-(2-methyl-1H-indol-5-yl)-3-phenyl-propionamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 18423184Ethyl acetate ethanol methanolSolvent

Procedure

To a solution of N-methyl-3-(2-methyl-1H-indol-5-yl)-3-phenyl-acrylamide LXVIII (990 mg, 3.41 mmol) in EtOH/EtOAc/MeOH (5/2/1, 40 ml) was added Pd/C (5%, 90 mg). The mixture was hydrogenated in a Parr apparatus at 60 psi of H2 for 48 hours. Degoussa-type catalyst (10% Pd/C, catalytic amount) was added to the mixture. The mixture was hydrogenated in a Parr apparatus at 60 psi of H2 for additional 6 hours. The reaction mixture was filtered through celite, and the filter cake was washed with MeOH, hot EtOH and DCM. The filtrate was concentrated affording N-methyl-3-(2-methyl-1H-indol-5-yl)-3-phenyl-propionamide LXIX as a light orange foamy solid in quantitative yield (1.05 g).

Workup

  1. waitThe mixture was hydrogenated in a Parr apparatus at 60 psi of H2 for additional 6 hours
  2. filtrationThe reaction mixture was filtered through celite
  3. washthe filter cake was washed with MeOH, hot EtOH and DCM
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f93e565156bd468699c89816d8038cb5
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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