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

HRID 71185노트

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HRID 71185 반응식
[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]([N:33]4[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]4)=[C:29]([O:39][CH3:40])[N: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[N: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[N:33]1[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 27779433,4,5-TrifluorophenolHCID 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

생성물 1

HCID 66603977ethyl 3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-8-(3,4,5-trifluorophenoxy)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate수율 41.4%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 25517Ammonium Chloride용매

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온도
100 °C

실험 절차

To a mixture of 3,4,5-trifluorophenol (0.31 g) and potassium carbonate (0.80 g) in DMF (16 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 (0.80 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, 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 (0.42 g).

후처리

  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 (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-0ac2b61a17124ac695ed9f7e8bbbf65f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822699B2

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