Reacción #1518622

Ecuación de reacción

2,4-dibromo-5,7-difluoro-3-methylquinoline

(1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine

potassium phosphate tribasic

piperidin-2-one

→

1-(4-bromo-5,7-difluoro-3-methylquinolin-2-yl)piperidin-2-one

Disolventes

1,4-dioxane

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with EtOAc (2×100 mL)
2. 2
   LavadoThe combined organic layers were washed with brine
3. 3
   Secadodried over magnesium sulfate
4. 4
   OtroThe crude product was then purified by medium pressure chromatography (silica, 0 to 100% EtOAc:hexanes)

Procedimiento

The 2,4-dibromo-5,7-difluoro-3-methylquinoline (2.000 g, 5.90 mmol), piperidin-2-one (590 mg, 5.90 mmol), copper (I) iodide (57.0 mg, 0.300 mmol), (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (0.094 mL, 0.59 mmol) and potassium phosphate tribasic (2.50 g, 11.9 mmol) were combined in 1,4-dioxane (10 mL) and stirred in the microwave reactor for 3.5 h. The reaction was diluted with water and extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine and dried over magnesium sulfate. The crude product was then purified by medium pressure chromatography (silica, 0 to 100% EtOAc:hexanes) to give 1-(4-bromo-5,7-difluoro-3-methylquinolin-2-yl)piperidin-2-one. Mass Spectrum (ESI) m/e=355.1 (M+1).

Fuente