Potassium Carbonate → Ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

HRID 71158Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 71158
[F:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([F:9])[C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].Cl[C:18]1([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:23][CH2:22][CH2:21][N:20]2[C:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33]4[O:37][C:36]([CH3:38])=[N:35][CH:34]=4)=[C:29]([O:39][CH3:40])[CH:28]=3)=[N:25][N:26]=[C:19]12>CN(C=O)C.C(OCC)(=O)C.[Cl-].[NH4+]>[CH3:40][O:39][C:29]1[CH:28]=[C:27]([C:24]2[N:20]3[CH2:21][CH2:22][CH2:23][C:18]([O:10][C:4]4[CH:3]=[C:2]([F:1])[C:7]([F:8])=[C:6]([F:9])[CH:5]=4)([C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:19]3=[N:26][N:25]=2)[CH:32]=[CH:31][C:30]=1[C:33]1[O:37][C:36]([CH3:38])=[N:35][CH:34]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 27779433,4,5-TrifluorophenolHCID 66604255Ethyl 8-chloro-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

Produkt 1

HCID 66608678Ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylateAusbeute 44,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 3,4,5-trifluorophenol (0.19 g) and potassium carbonate (0.50 g) in DMF (5 mL) was added ethyl 8-chloro-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (0.50 g) at room temperature, and the mixture was stirred at 100° C. for 30 min. The reaction mixture was allowed to cool to room temperature, 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 (NH, ethyl acetate/hexane) to give the title compound (0.28 g).

Aufarbeitung

  1. temperatureto cool 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 (NH, ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ee60824471aa49b2a03ff935c1066ff0
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822699B2

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