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 2106020ノート

反応式

HRID 2106020 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
85 °C

実験手順

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.

後処理

  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))

出典と根拠

ORDレコード
ord-2828e90cb9e0497c820579193ae2279a
出典データセット
uspto-grants-2009_08
特許番号
US07579469B2

反応ノート

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