5-Nitro-7-azaindole → 1H-pyrrolo(2,3-b)pyridin-5-amine

HRID 2222583Notes

Reaction equation

HRID 2222583 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1)([O-])=O>C(OCC)(=O)C>[NH:10]1[C:7]2=[N:8][CH:9]=[C:4]([NH2:1])[CH:5]=[C:6]2[CH:12]=[CH:11]1

Participants

3

Reactant 1

HCID 115211405-Nitro-7-azaindole

Product 1

HCID 117151871H-pyrrolo(2,3-b)pyridin-5-amineYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-nitro-1H-pyrrolo[2,3-b]pyridine (0.4 g, 2.45 mmol) in ethyl acetate (100 mL) 5% Pd—C (0.3 g) was added and the mixture subdued to hydrogenation (30 psi) in a Parr apparatus. After 4 hours the catalyst was filtered off through celite, the cake was washed with ethyl acetate and then with a mixture of dichloromethane/methanol 4:1. 1H-pyrrolo[2,3-b]pyridin-5-amine (5-aminoazaindole) was obtained in 95% yield (0.31 g, 2.33 mmol).

Workup

  1. filtrationAfter 4 hours the catalyst was filtered off through celite
  2. washthe cake was washed with ethyl acetate
  3. additionwith a mixture of dichloromethane/methanol 4:1

Sources & evidence

ORD record
ord-52e2cf42b12f4ce3ae81bc9059929425
Source dataset
uspto-grants-2008_05
Patent number
US07371862B2

Reaction notes

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