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

HRID 1014332Notes

Reaction equation

HRID 1014332 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 59441930(2R)-N,N-dimethyl-1-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]-1-oxo-2-propanamine

Product 1

HCID 594417621-[(2R)-2-(dimethylamino)propanoyl]-5-(methyloxy)-2,3-dihydro-1H-indol-6-amineYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R)-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 maintained under 50 psi of H2(g) overnight on the Fisher-Porter. The crude material was filtered through a celite pad, washed with ethyl acetate, concentrated on the rotovap, and placed under high vacuum overnight to afford 1-[(2R)-2-(dimethylamino)propanoyl]-5-(methyloxy)-2,3-dihydro-1H-indol-6-amine (1.4 g, 71%). ESIMS (M+H)+=264.

Workup

  1. temperaturethe reaction maintained under 50 psi of H2(g) overnight on the Fisher-Porter
  2. filtrationThe crude material was filtered through a celite pad
  3. washwashed with ethyl acetate
  4. concentrationconcentrated on the rotovap
  5. customplaced under high vacuum overnight

Sources & evidence

ORD record
ord-02269c417f124c17b0f7a7a5cd3a9997
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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