Potassium Carbonate → ethyl 8-(3,4-difluorophenoxy)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

HRID 71186

Reaktionsgleichung

Reaktionsgleichung von HRID 71186
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].Cl[C:17]1([C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:22][CH2:21][CH2:20][N:19]2[C:23]([C:26]3[CH:31]=[CH:30][C:29]([N:32]4[CH:36]=[C:35]([CH3:37])[N:34]=[CH:33]4)=[C:28]([O:38][CH3:39])[N:27]=3)=[N:24][N:25]=[C:18]12>CN(C=O)C.C(OCC)(=O)C.[Cl-].[NH4+]>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[O:9][C:17]1([C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:22][CH2:21][CH2:20][N:19]2[C:23]([C:26]3[CH:31]=[CH:30][C:29]([N:32]4[CH:36]=[C:35]([CH3:37])[N:34]=[CH:33]4)=[C:28]([O:38][CH3:39])[N:27]=3)=[N:24][N:25]=[C:18]12

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 759273,4-DifluorophenolHCID 66607848ethyl 8-chloro-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

Produkt 1

HCID 66608451ethyl 8-(3,4-difluorophenoxy)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylateAusbeute 49,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 3,4-difluorophenol (59 mg) and potassium carbonate (0.18 g) in DMF (4 mL) was added ethyl 8-chloro-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (0.18 g) at room temperature, and the mixture was stirred at 100° C. for 30 min. The reaction mixture was cooled to room temperature, and diluted with ethyl acetate and saturated aqueous ammonium chloride solution, the mixture was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.11 g).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washthe mixture was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0b7c7b3ab34c432fba5d4a5e74ce8bf6
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822699B2

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