methyl 5-(4-((3-nitrophenyl)amino)pyridin-2-yl)-1H-pyrrole-3-carboxylate → methyl 5-(4-((3-aminophenyl)amino)pyridin-2-yl)-1H-pyrrole-3-carboxylate

HRID 521767

Reaktionsgleichung

Reaktionsgleichung von HRID 521767
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([C:17]3[NH:21][CH:20]=[C:19]([C:22]([O:24][CH3:25])=[O:23])[CH:18]=3)[CH:12]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>CCOC(C)=O.CCO>[NH2:1][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([C:17]3[NH:21][CH:20]=[C:19]([C:22]([O:24][CH3:25])=[O:23])[CH:18]=3)[CH:12]=2)[CH:7]=[CH:8][CH:9]=1

Komponenten

3

Edukt 1

HCID 67042295methyl 5-(4-((3-nitrophenyl)amino)pyridin-2-yl)-1H-pyrrole-3-carboxylate

Produkt 1

HCID 67042564methyl 5-(4-((3-aminophenyl)amino)pyridin-2-yl)-1H-pyrrole-3-carboxylateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584252Ethanol ethylacetateLösungsmittel

Versuchsvorschrift

Methyl 5-(4-((3-nitrophenyl)amino)pyridin-2-yl)-1H-pyrrole-3-carboxylate (1.32 g, 3.9 mmol) was taken up in EtOAc/EtOH (1:1; 90 mL) and purged with N2. Pd/C (10%, 0.145 g) was added and the mixture was stirred under an atmosphere of H2 at rt for 18 h. The mixture was filtered over celite, washing with EtOAc/EtOH. The filtrate was concentrated, taken back up in EtOAc and filtered over celite again to remove any residual catalyst. The filtrate was concentrated again and taken back up in EtOAc. The solution was filtered and the filtrate was concentrated to afford a tan solid. The solid was washed with CH2Cl2/hexanes (1:2) and dried under high vacuum to afford methyl 5-(4-((3-aminophenyl)amino)pyridin-2-yl)-1H-pyrrole-3-carboxylate (1.15 g, 96% yield) as a tan solid.

Aufarbeitung

  1. custompurged with N2
  2. additionPd/C (10%, 0.145 g) was added
  3. filtrationThe mixture was filtered over celite
  4. washwashing with EtOAc/EtOH
  5. concentrationThe filtrate was concentrated
  6. filtrationfiltered over celite again
  7. customto remove any residual catalyst
  8. concentrationThe filtrate was concentrated again
  9. filtrationThe solution was filtered
  10. concentrationthe filtrate was concentrated
  11. customto afford a tan solid
  12. washThe solid was washed with CH2Cl2/hexanes (1:2)
  13. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c76ba6c860a4497788c898491266d028
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328103B2

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