Reacción #43333

ord-f177d71729334e70bce27de2868c1f16

Ecuación de reacción

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
Rendimiento 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
Rendimiento 53.0%

Disolventes

Condiciones de reacción

Temperatura
80°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Lavadoby washing with water and saturated brine
  2. 2
    Secadodrying over anhydrous sodium sulfate
  3. 3
    ConcentraciónConcentrating
  4. 4
    Otrothe reaction liquid under reduced pressure
  5. 5
    Otrothe residue was purified on silica gel column chromatography (C-300; methanol:chloroform=1:20-1:10)

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07732456B2uspto-grants-2010_06