3,3-Dimethyl-1-(3-nitropyridin-2-yl)-2,3-dihydro-1H-indole → 2-(3,3-Dimethylindolin-1-yl)pyridin-3-amine

HRID 2192222Notes

Reaction equation

HRID 2192222 reaction equation
[CH3:1][C:2]1([CH3:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]2[C:16]([N+:17]([O-])=O)=[CH:15][CH:14]=[CH:13][N:12]=2)[CH2:3]1>CO.[Pd]>[CH3:1][C:2]1([CH3:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]2[C:16]([NH2:17])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH2:3]1

Participants

4

Reactant 1

HCID 574233113,3-Dimethyl-1-(3-nitropyridin-2-yl)-2,3-dihydro-1H-indole

Product 1

HCID 574233122-(3,3-Dimethylindolin-1-yl)pyridin-3-amineYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4a (30 mg, 0.111 mmol) in MeOH was added 10% Pd/C (10 mg). The reaction mixture was stirred at rt under H2 for 2 h. The catalyst was filtered through a cake of Celite® and the filtrate was evaporated under reduced pressure to afford 4b (20 mg, 76%) as a yellowish powder. MS (ES) m/z 240 [M+H]+.

Workup

  1. filtrationThe catalyst was filtered through a cake of Celite®
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-de37e8afd7dc49b5986c9bf5cf2c0531
Source dataset
uspto-grants-2012_12
Patent number
US08329718B2

Reaction notes

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