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

HRID 1402483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1402483
C(OC([N:8]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=1)[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2[NH:19][CH:18]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:16]=2)[CH:10]=1)=O)(C)(C)C>C1(C)C=CC=CC=1>[N+:30]([C:26]1[CH:25]=[C:24]([NH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[NH:19][CH:18]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:16]=3)[CH:10]=2)[CH:29]=[CH:28][CH:27]=1)([O-:32])=[O:31]

Komponenten

3

Edukt 1

HCID 67042276methyl 5-(4-(tert-butoxycarbonyl(3-nitrophenyl)amino)pyridine-2-yl)-1H-pyrrole-3-carboxylate

Produkt 1

HCID 67042295methyl 5-(4-((3-nitrophenyl)amino)pyridin-2-yl)-1H-pyrrole-3-carboxylateAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Methyl 5-(4-(tert-butoxycarbonyl(3-nitrophenyl)amino)pyridine-2-yl)-1H-pyrrole-3-carboxylate (0.40 g, 0.91 mmol) was taken up in toluene (38 mL) and SiO2 (9.0 g) was added. The mixture stirred at reflux for 20 h. The mixture was cooled to rt and filtered over celite, washing with EtOAc. The filtrate was concentrated to a bright orange color. The solid was taken up in hexanes and filtered. The solid was then washed with CH2Cl2/hexanes to afford methyl 5-(4-((3-nitrophenyl)amino)pyridin-2-yl)-1H-pyrrole-3-carboxylate (0.15 g, 49% yield) as a bright yellow solid.

Aufarbeitung

  1. temperatureat reflux for 20 h
  2. filtrationfiltered over celite
  3. washwashing with EtOAc
  4. concentrationThe filtrate was concentrated to a bright orange color
  5. filtrationfiltered
  6. washThe solid was then washed with CH2Cl2/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f1a56518ef834058809cc8a860739325
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906944B2

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