Reacción #452702

Ecuación de reacción

ethyl 4-bromobenzoate

(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)amine

Compound 19

(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)amine

cesium carbonate

→

title compound

Rendimiento 56.0%

Ethyl [(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)amino)benzoate

Rendimiento 56.0%

Disolventes

water

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was then cooled to room temperature
2. 2
   Extracciónextracted with ethyl ether (2×)
3. 3
   LavadoThe combined organic extracts were washed with brine
4. 4
   Secadodried (MgSO4)
5. 5
   ConcentraciónThe filtered solution was concentrated under reduced pressure
6. 6
   Otrothe crude product was purified by silica gel chromatography (10% ethyl acetate in hexanes)

Procedimiento

To a solution of ethyl 4-bromobenzoate (0.98 g, 4.3 mmol) and (1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)amine (Compound 19, 0.69 g, 3.0 mmol) in 15.0 mL of toluene stirring under argon was added cesium carbonate (1.84 g, 5.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (35 mg, 0.04 mmol) and BINAP (68 mg, 0.11 mmol) consecutively. The reaction mixture was then heated at 100° C. for 48 hours. The reaction mixture was then cooled to room temperature, diluted with water and extracted with ethyl ether (2×). The combined organic extracts were washed with brine and dried (MgSO4). The filtered solution was concentrated under reduced pressure and the crude product was purified by silica gel chromatography (10% ethyl acetate in hexanes) to give the title compound (0.63 g, 56% 2 steps) as an orange solid.

Fuente