1-ethyl-2-(4-methylphenyl)-5-nitro-1H-pyrrolo[2,3-b]pyridine → 1-ethyl-2-(4-methylphenyl)-1H-pyrrolo[2,3-b]pyridin-5-amine

HRID 1947424Notes

Reaction equation

HRID 1947424 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=[C:6]2[CH:5]=[C:4]1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[CH3:2]>CCOC(C)=O.CCO>[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([NH2:12])[CH:11]=[C:6]2[CH:5]=[C:4]1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[CH3:2]

Participants

3

Reactant 1

HCID 672852781-ethyl-2-(4-methylphenyl)-5-nitro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 672850961-ethyl-2-(4-methylphenyl)-1H-pyrrolo[2,3-b]pyridin-5-amine

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of 1-ethyl-2-(4-methylphenyl)-5-nitro-1H-pyrrolo[2,3-b]pyridine (0.36 g, 1.3 mmol) in a EtOAc/EtOH (absolute)=4:7 mixture (110 ml) was hydrogenated in H2 atmosphere with the presence of 10% Pd(C) (110 mg) for 2 h. The residue was filtered under vacuum through Celite to remove the catalyst and the solvent evaporated to give crude 1-ethyl-2-(4-methylphenyl)-1H-pyrrolo[2,3-b]pyridin-5-amine which was used without any further purification:

Workup

  1. customfor 2 h
  2. filtrationThe residue was filtered under vacuum through Celite
  3. customto remove the catalyst
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-0a298ebd3396484688ea0505d94d0007
Source dataset
uspto-grants-2013_03
Patent number
US08399477B2

Reaction notes

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