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 1402484ノート

反応式

HRID 1402484 の反応式
[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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21584252Ethanol ethylacetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-afc531f2f504441e8ddb9e053230f0e2
出典データセット
uspto-grants-2014_12
特許番号
US08906944B2

反応ノート

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