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

HRID 1716678Notes

Reaction equation

HRID 1716678 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][CH:16]=[C:15]2[CH3:21])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CCO.CCOC(C)=O.C(Cl)Cl.[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][CH:16]=[C:15]2[CH3:21])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 67355796N-Methyl-3-(3-methyl-1H-indol-5-yl)-3-phenyl-acrylamide

Product 1

HCID 59831672N-Methyl-3-(3-methyl-1H-indol-5-yl)-3-phenyl-propionamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22027680Ethanol ethyl acetate methylene chlorideSolvent

Procedure

To a solution of N-methyl-3-(3-methyl-1H-indol-5-yl)-3-phenyl-acrylamide LXXII (386 mg, 1.33 mmol) in EtOH/EtOAc/DCM (2/1.5/1, 55 ml) was added Degoussa-type catalyst (Pd/C 10%, 40 mg), and the mixture was hydrogenated in a Parr apparatus at 50 psi of H2 for 20 hours. The reaction mixture was filtered through celite, and the filter cake was washed with MeOH, EtOAc and DCM. The filtrate was concentrated to afford N-Methyl-3-(3-methyl-1H-indol-5-yl)-3-phenyl-propionamide LXXIII as a white foamy solid (341 mg, 89% yield).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe filter cake was washed with MeOH, EtOAc and DCM
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e1b42ccc089b4d7d9fecfa706a7742f8
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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