反応 #43333

ord-f177d71729334e70bce27de2868c1f16

反応方程式

O=C([O-])[O-].[K+].[K+]
Potassium carbonate
COS(=O)(=O)c1ccc(C)cc1
methyl p-toluenesulfonate
CN(C)C=O
DMF
O=c1ccccn1-c1ccc(OCCN2CCCC2)cc1
1-{4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-1H-pyridin-2-one
COc1ccc(/C=C/c2ccn(-c3ccc(OCCN4CCCC4)cc3)c(=O)c2)cc1
title compound
収率 53.0%
COc1ccc(/C=C/c2ccn(-c3ccc(OCCN4CCCC4)cc3)c(=O)c2)cc1
4-[(E)-2-(4-methoxyphenyl)vinyl]-1-{4-[2-(1-pyrrolidinyl]-ethoxy}phenyl)-1H-pyridin-2-one
収率 53.0%

反応条件

温度
80°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    洗浄by washing with water and saturated brine
  2. 2
    乾燥drying over anhydrous sodium sulfate
  3. 3
    濃縮Concentrating
  4. 4
    その他the reaction liquid under reduced pressure
  5. 5
    その他the residue was purified on silica gel column chromatography (C-300; methanol:chloroform=1:20-1:10)

実験手順

Potassium carbonate (11 mg, 0.08 mmol) and methyl p-toluenesulfonate (6 mg, 0.03 mmol) were added to DMF (2 mL) solution of 4-[(E)-2-4-hydroxyphenyl)vinyl]-1-{4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-1H-pyridin-2-one (11 mg, 0.03 mmol), and stirred for a day and night at 80° C. Ethyl acetate was added to the reaction liquid, followed by washing with water and saturated brine and drying over anhydrous sodium sulfate. Concentrating the reaction liquid under reduced pressure, the residue was purified on silica gel column chromatography (C-300; methanol:chloroform=1:20-1:10) to provide the title compound (6 mg, 53%) as a white solid.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07732456B2uspto-grants-2010_06