Reacción #155351

Ecuación de reacción

Sodium triacetoxyborohydride

1-(2-Pyridyl)piperazine

5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydroquinoline-2-carbaldehyde

→

5-fluoro-3-(4-methoxyphenyl)-8-propoxy-2-(4-pyridin-2-yl-piperazin-1-ylmethyl)-1H-quinolin-4-one

Rendimiento 35.4%

Disolventes

Dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred at room temperature for 4 hours
2. 2
   Lavadowashed with water
3. 3
   Secadothe mixture was dried over sodium sulfate
4. 4
   OtroThereafter, the solvent was removed under reduced pressure
5. 5
   OtroThe residue was then purified
6. 6
   OtroThe solvent was removed under reduced pressure
7. 7
   Otrothe residue was recrystallized from ethyl acetate-n-hexane

Procedimiento

1-(2-Pyridyl)piperazine (551 mg, 3.38 mmol) was added to a 1,2-dichloromethane solution (20 ml) of 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydroquinoline-2-carbaldehyde (800 mg, 2.25 mmol) and stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (670 mg, 3.16 mmol) was added to the resulting mixture and stirred at room temperature for 4 hours. Dichloromethane was added to the resulting reaction mixture, washed with water, and then the mixture was dried over sodium sulfate. Thereafter, the solvent was removed under reduced pressure. The residue was then purified using NH silica gel column chromatography (dichloromethane:ethyl acetate=1:1). The solvent was removed under reduced pressure and the residue was recrystallized from ethyl acetate-n-hexane, giving a white powder of 5-fluoro-3-(4-methoxyphenyl)-8-propoxy-2-(4-pyridin-2-yl-piperazin-1-ylmethyl)-1H-quinolin-4-one (400 mg, yield: 35%).

Fuente