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

HRID 623696노트

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HRID 623696 반응식
[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

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 147614424-Chloro-2-(trifluoromethyl)pyridineHCID 901108372-(4-fluorophenyl)-2,3-dihydro-5-methyl-4H-1,2,3-triazol-4-one2회

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1b4c6226f4a74d8eb59ad27880081edf
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302999B2

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