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 491651Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 491651
[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

Komponenten

4

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 21584252Ethanol ethylacetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-3e6d196ea61c4b22a95143692986d87c
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531553B2

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