Potassium Carbonate → Ethyl 2-(4-phenyl-1H-imidazol-1-yl)pyridine-3-carboxylate

HRID 12425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 12425
Cl[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:13]1([C:19]2[N:20]=[CH:21][NH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[C:13]1([C:19]2[N:20]=[CH:21][N:22]([C:2]3[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:9][CH:10]=[CH:11][N:12]=3)[CH:23]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 2796614Ethyl chloronicotinateHCID 178418822HCID 178418822, Verbindung

Produkt 1

HCID 66720067Ethyl 2-(4-phenyl-1H-imidazol-1-yl)pyridine-3-carboxylateAusbeute 28,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2855718-Crown-6KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. concentrationby concentrating
  2. washwashing with water and sat. NaCl solution
  3. dry with materialdrying over MgSO4
  4. filtrationfiltering
  5. customevaporating

Quellen und Nachweise

ORD-Eintrag
ord-36f46d1507004530b03063bb98e56d46
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728012B2

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