Reacción #69983

Ecuación de reacción

4-[1-(4-bromophenyl)piperidin-4-yloxy]pyridine

sodium tert-butoxide

ethyl acetate

3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester

→

4-{4-[4-(pyridin-4-yloxy)piperidin-1-yl]phenyl}-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester

Rendimiento 62.8%

Disolventes

o-xylene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONaddition
2. 2
   TemperaturaHeating
3. 3
   Otrois brought back to ambient temperature
4. 4
   LavadoThe mixture is washed twice with water
5. 5
   SecadoThe organic phase is dried over sodium sulphate
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroThe crude product obtained
8. 8
   Otrois chromatographed on silica gel, elution

Procedimiento

1.2 g of 4-[1-(4-bromophenyl)piperidin-4-yloxy]pyridine are placed in 20 ml of anhydrous o-xylene. 0.844 g of 3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester is added, then 0.519 g of sodium tert-butoxide is added, followed by 0.032 g of palladium acetate, and then addition is completed with 0.029 g of tri(tert-butyl)phosphine. The reaction mixture is heated at 150° C. for 6 h. Heating is subsequently halted, the mixture is brought back to ambient temperature and ethyl acetate is added. The mixture is washed twice with water and then twice with a saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulphate and concentrated under reduced pressure. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of a dichloromethane/methanol (99/1 to 97/3) mixture. 1.1 g of 4-{4-[4-(pyridin-4-yloxy)piperidin-1-yl]phenyl}-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester are obtained.

Fuente