4-(3,4-dinitro-phenoxy)-1H-pyrrolo[2,3-b]pyridine → 4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-benzene-1,2-diamine

HRID 491651Notes

Reaction equation

HRID 491651 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][C:19]=1[N+:20]([O-])=O)[O:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[NH:14][CH:15]=[CH:16][C:9]=12)([O-])=O>[Pd].CCO.CCOC(C)=O>[NH:14]1[C:10]2=[N:11][CH:12]=[CH:13][C:8]([O:7][C:6]3[CH:5]=[C:4]([NH2:1])[C:19]([NH2:20])=[CH:18][CH:17]=3)=[C:9]2[CH:16]=[CH:15]1

Participants

4

Reactant 1

HCID 177564904-(3,4-dinitro-phenoxy)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 177564944-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of 4-(3,4-dinitro-phenoxy)-1H-pyrrolo[2,3-b]pyridine (Step C, 0.284 g, 0.95 mmol) in a 2/1 EtOH/EtOAc (30 mL) mixture with a catalytic amount of 10% Pd/C was stirred under H2 at RT and atmospheric pressure. The catalyst was removed by filtration and the solvents were removed under vacuum. The crude material was purified on silica gel using a CH2Cl2/EtOH/NH4OH gradient (100/0/0 to 90/10/1) to give 4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)-benzene-1,2-diamine.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvents were removed under vacuum
  3. customThe crude material was purified on silica gel using a CH2Cl2/EtOH/NH4OH gradient (100/0/0 to 90/10/1)

Sources & evidence

ORD record
ord-3e6d196ea61c4b22a95143692986d87c
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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