Potassium Carbonate → 4-[[2-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl]oxy]-2-(trifluoromethyl)pyridine

HRID 623696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 623696
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[NH:12][C:11](=[O:13])[C:10]([CH3:14])=[N:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:22]1[CH:27]=[CH:26][N:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1>CN(C)C=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[N:12]=[C:11]([O:13][C:22]3[CH:27]=[CH:26][N:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)[C:10]([CH3:14])=[N:9]2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 147614424-Chloro-2-(trifluoromethyl)pyridineHCID 901108372-(4-fluorophenyl)-2,3-dihydro-5-methyl-4H-1,2,3-triazol-4-one2×

Produkt 1

HCID 901102114-[[2-(4-fluorophenyl)-5-methyl-2H-1,2,3-triazol-4-yl]oxy]-2-(trifluoromethyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 2-(4-fluorophenyl)-2,3-dihydro-5-methyl-4H-1,2,3-triazol-4-one (i.e. the product of Step C, 3.1 g, 16 mmol) in N,N-dimethylformamide (70 mL) was added anhydrous potassium carbonate (6.2 g, 45 mmol) under an atmosphere of nitrogen. 4-Chloro-2-trifluoromethyl-pyridine (2.9 g, 16 mmol) was added and the mixture was heated to 100° C. for 20 h. The reaction mixture was diluted with water, then extracted with diethyl ether. The organic layer was washed successively with water and saturated aqueous sodium chloride solution, dried (MgSO4), filtered, and concentrated under reduced pressure. The crude material was purified by chromatography on silica gel eluting with 0 to 20% ethyl acetate in hexanes to obtain the title compound (4.2 g) as a viscous light yellow oil that solidified upon standing to form an off-white solid.

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed successively with water and saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by chromatography on silica gel eluting with 0 to 20% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-1b4c6226f4a74d8eb59ad27880081edf
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09302999B2

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