Potassium Carbonate → Ethyl 8-(3,4-difluorophenoxy)-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

HRID 1398185

반응식

HRID 1398185 반응식
[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]([C:32]4[O:36][C:35]([CH3:37])=[N:34][CH:33]=4)=[C:28]([O:38][CH3:39])[CH: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]([C:32]4[O:36][C:35]([CH3:37])=[N:34][CH:33]=4)=[C:28]([O:38][CH3:39])[CH:27]=3)=[N:24][N:25]=[C:18]12

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 759273,4-DifluorophenolHCID 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

생성물 1

HCID 66609151Ethyl 8-(3,4-difluorophenoxy)-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-carboxylate수율 44.1%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 25517Ammonium Chloride용매

반응 조건

온도
100 °C

실험 절차

To a mixture of 3,4-difluorophenol (0.16 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, 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 (0.27 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-2320b7d140794bf7885e6eb127da91c4
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901309B2

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