Reacción #1004857

Ecuación de reacción

acetic acid

6-chloro-quinoline

1-(6-methyl-pyridin-2-yl)-ethanone

potassium tert-butoxide

→

1-(6-Methyl-pyridin-2-yl)-2-quinolin-6-yl-ethanone

Rendimiento 78.1%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction mixture
2. 2
   Temperaturacooled down to 20° C.
3. 3
   FiltraciónThe resulting solids were filtered off
4. 4
   Concentraciónthe mother liquor was concentrated in vacuo

Procedimiento

To a solution of 6-chloro-quinoline (2.08 g, 12.3 mmol) in tetrahydrofuran (50 mL) was added 1-(6-methyl-pyridin-2-yl)-ethanone (2.0 g, 14.8 mmol, 1.1 equiv), palladium acetate (0.055 g, 0.25 mmol, 0.02 equiv), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (0.197 g, 0.50 mmol, 0.04 equiv), and potassium tert-butoxide (3.76 g, 30.75 mmol, 2.2 equiv). The resulting reaction mixture was heated to 80° C. for 18 hours, then cooled down to 20° C., and slowly treated with acetic acid (3 mL). The resulting solids were filtered off, and the mother liquor was concentrated in vacuo. Silica gel chromatography (3:1 hexane/acetone) yielded 1-(6-Methyl-pyridin-2-yl)-2-quinolin-6-yl-ethanone (2.52 g, 78%).

Fuente