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 521767노트

반응식

HRID 521767 반응식
[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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 21584252Ethanol ethylacetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c76ba6c860a4497788c898491266d028
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328103B2

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