3-Chloro-5-(trifluoromethyl)pyridin-2-ol → 3-chloro-1-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-5-trifluoromethyl-1H-pyridin-2-one

HRID 2106020노트

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HRID 2106020 반응식
[Cl:1][C:2]1[C:3]([OH:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[O-]CC.[Na+].[F:17][C:18]1[CH:19]=[CH:20][C:21]([O:35][CH3:36])=[C:22]([C:24]([CH3:34])([CH3:33])[CH2:25][C:26]2([C:29]([F:32])([F:31])[F:30])[CH2:28][O:27]2)[CH:23]=1>CCO>[Cl:1][C:2]1[C:3](=[O:12])[N:4]([CH2:28][C:26]([OH:27])([C:29]([F:30])([F:32])[F:31])[CH2:25][C:24]([C:22]2[CH:23]=[C:18]([F:17])[CH:19]=[CH:20][C:21]=2[O:35][CH3:36])([CH3:33])[CH3:34])[CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

참가 물질

5

반응물 3

HCID 7254363-Chloro-5-(trifluoromethyl)pyridin-2-olHCID 2723922Sodium ethoxideHCID 160992392-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

생성물 1

HCID 578098453-chloro-1-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-5-trifluoromethyl-1H-pyridin-2-one

시약·촉매·용매 1

HCID 702Ethanol용매2회

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온도
85 °C

실험 절차

A mixture of 3-chloro-5-trifluoromethylpyridin-2-ol (135 mg, 0.68 mmol) in 1 mL of EtOH was added to 0.13 mL of a 1M sodium ethoxide solution in ethanol and was heated to 85° C. for 5 minutes in a sealed vial. The mixture was cooled to room temperature, 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane was added, and the mixture heated to 85° C. overnight in a sealed vial. The volatiles were removed in vacuo and the residue diluted with water and extracted with EtOAc. The organic extracts were combined, dried over sodium sulfate and concentrated in vacuo. The residue was purified on PLC plate (hexanes-EtOAc (8:2)) to give 125 mg of 3-chloro-1-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-5-trifluoromethyl-1H-pyridin-2-one as a solid.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. temperaturethe mixture heated to 85° C. overnight in a sealed vial
  3. customThe volatiles were removed in vacuo
  4. additionthe residue diluted with water
  5. extractionextracted with EtOAc
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified on PLC plate (hexanes-EtOAc (8:2))

출처 및 근거

ORD 기록
ord-2828e90cb9e0497c820579193ae2279a
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07579469B2

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