Reaktion #40703

ord-36f46d1507004530b03063bb98e56d46

Reaktionsgleichung

CCOC(=O)c1cccnc1Cl
ethyl 2-chloronicotinate
c1ccc(-c2c[nH]cn2)cc1
4-phenylimidazole
O=C([O-])[O-].[K+].[K+]
K2CO3
CCOC(=O)c1cccnc1-n1cnc(-c2ccccc2)c1
dark oil
Ausbeute 28.9%
CCOC(=O)c1cccnc1-n1cnc(-c2ccccc2)c1
Ethyl 2-(4-phenyl-1H-imidazol-1-yl)pyridine-3-carboxylate
Ausbeute 28.9%

Lösungsmittel

Reaktionsbedingungen

Temperatur
160°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenby concentrating
  2. 2
    Waschenwashing with water and sat. NaCl solution
  3. 3
    Trocknendrying over MgSO4
  4. 4
    Filtrationfiltering
  5. 5
    Sonstigeevaporating

Vorschrift

A mixture of 5.0 g of ethyl 2-chloronicotinate (26.94 mmol), 3.4 g of 4-phenylimidazole (23.58 mmol), 7.6 g of K2CO3 and 80 mg of 18-crown-6 in 18 ml of N,N-dimethylformamide was heated in a microwave at 160° C. for about 1 hour. This was followed by concentrating, taking up the residue in dichloromethane, washing with water and sat. NaCl solution, drying over MgSO4, filtering and evaporating. Chromatography on silica gel (eluent: CH2Cl2/methanol 2%-5%) resulted in 2 g of a dark oil, which was immediately reacted further; ESI-MS [M+H]+=294.15.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07728012B2uspto-grants-2010_06