2-nitro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-phenol → 2-Amino-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-phenol

HRID 491690Notes

Reaction equation

HRID 491690 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]3[NH:17][CH:18]=[CH:19][C:12]=23)[CH:7]=[CH:6][C:5]=1[OH:20])([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]3[NH:17][CH:18]=[CH:19][C:12]=23)[CH:7]=[CH:6][C:5]=1[OH:20]

Participants

4

Reactant 1

HCID 576784942-nitro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-phenol

Product 1

HCID 576785092-Amino-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Nitro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-phenol (Step c, 3 g, 11.1 mmol) was dissolved into MeOH (100 mL) and the atmosphere was replaced by argon. A catalytic amount of 10% Pd/C was added and the argon was replaced by a H2 atmosphere. The mixture was stirred for 16 h at RT at balloon pressure. The Pd/C was filtered and the obtained 2-amino-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-phenol was used crude in the next step.

Workup

  1. filtrationThe Pd/C was filtered

Sources & evidence

ORD record
ord-c36ce304be0f4a6aaff1bc26daa6c93f
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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