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 1915048Notes

Reaction equation

HRID 1915048 reaction equation
[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

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3a8802fd73a84e9daee16077f80c571c
Source dataset
uspto-grants-2013_12
Patent number
US08614234B2

Reaction notes

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