(2S)-N,N-dimethyl-1-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-1-oxo-2-propanamine → 1-[(2S)-2-(dimethylamino)propanoyl]-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine

HRID 1014334Notes

Reaction equation

HRID 1014334 reaction equation
[CH3:1][N:2]([CH3:21])[C@@H:3]([CH3:20])[C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([N+:15]([O-])=O)[CH:13]=2)[CH2:8][CH2:7]1)=[O:5]>C(OCC)(=O)C.[Pd]>[CH3:1][N:2]([CH3:21])[C@@H:3]([CH3:20])[C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[C:12]([NH2:15])[CH:13]=2)[CH2:8][CH2:7]1)=[O:5]

Participants

4

Reactant 1

HCID 59442085(2S)-N,N-dimethyl-1-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-1-oxo-2-propanamine

Product 1

HCID 594417711-[(2S)-2-(dimethylamino)propanoyl]-5-(methyloxy)-2,3-dihydro-1H-indol-6-amineYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S)-N,N-dimethyl-1-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-1-oxo-2-propanamine (2.2 g, 7.50 mmol) in Ethyl acetate (250 mL) was added Pd/C (0.798 g, 0.750 mmol) and the reaction was maintained under 50 psi of H2(g) overnight on the Fisher-Porter apparatus. The reaction was filtered through a celite pad which was washed with ethyl acetate, concentrated by rotary evaporation, and high maintained under vacuum for 12 hours to afford 1-[(2S)-2-(dimethylamino)propanoyl]-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine (1.5 g, 76%). ESIMS (M+H)+=264.

Workup

  1. temperaturethe reaction was maintained under 50 psi of H2(g) overnight on the Fisher-Porter apparatus
  2. filtrationThe reaction was filtered through a celite pad which
  3. washwas washed with ethyl acetate
  4. concentrationconcentrated by rotary evaporation
  5. temperaturehigh maintained under vacuum for 12 hours

Sources & evidence

ORD record
ord-f4bf23754e5a46188666958d7123e1a0
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…