Potassium Carbonate → 4-Chloro-1-(5-ethoxycarbonylpyrid-2-yl)-2-methylimidazo[4,5-c]pyridine

HRID 1460319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1460319
[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.Cl[C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[N:10]([C:13]3[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=3)[C:6]=2[CH:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2799611Ethyl 6-chloronicotinateHCID 198771904-Chloro-2-methyl-3H-imidazo[4,5-c]pyridine

Produkt 1

HCID 198771824-Chloro-1-(5-ethoxycarbonylpyrid-2-yl)-2-methylimidazo[4,5-c]pyridineAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Chloro-2-methylimidazo[4,5-c]pyridine described in C.A. 79, 105515f but made by the method of Chem. Pharm. Bull, 12 (8) 866-872 (1964) (3.34 g, 20 mmol), and ethyl 6-chloronicotinate (3.71 g, 26.2 mmol) were dissolved in N,N-dimethylformamide (42 ml). Potassium carbonate (2.76 g, 20 mmol) was added and the reaction was refluxed overnight. The reaction mixture was cooled, the solvent removed under reduced pressure and the crude product purified by flash chromatography eluting with ethyl acetate. Fractions containing product were evaporated and the resulting foam triturated with ether. The solid was filtered and dried under reduced pressure yielding the title compound as a yellow solid (3.2 g, 51%).

Aufarbeitung

  1. temperaturethe reaction was refluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent removed under reduced pressure
  4. customthe crude product purified by flash chromatography
  5. washeluting with ethyl acetate
  6. additionFractions containing product
  7. customwere evaporated
  8. customthe resulting foam triturated with ether
  9. filtrationThe solid was filtered
  10. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-71d0fce18092421b83b4be0e915e7951
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05070205

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