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 521766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 521766
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-adeac8f50f4f46cfbc7d508fc70d2b46
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328103B2

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