Reacción #682936

Ecuación de reacción

2,6-dichloro-3-iodopyridine

(E)-2-(2-ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

→

(E)-2,6-dichloro-3-(2-ethoxyvinyl)pyridine

Rendimiento 86.0%

Disolventes

1,4-dioxane

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was cooled
2. 2
   Filtraciónfiltered through a pad of the celite
3. 3
   Lavadowashed with ethyl acetate
4. 4
   OtroThe combined filtrate was evaporated in vacuo
5. 5
   OtroThe resulting residue was purified
6. 6
   Lavadocolumn chromatography (eluted with 0-20% EtOAc/DCM)

Procedimiento

To a degassed solution of 2,6-dichloro-3-iodopyridine (3.0 g, 11 mmol) and (E)-2-(2-ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.2 g, 11 mmol) in 1,4-dioxane (20 mL) and water (1.0 mL) was added CS2CO3 (7.1 g, 22 mmol) and 1,1′-bis(di-tert-butylphosphino)ferrocene palladium chloride (357 mg, 0.54 mmol) under N2 protection. The resulting mixture was heated to 70° C. and stirred at this temperature overnight. The reaction was cooled, filtered through a pad of the celite and washed with ethyl acetate. The combined filtrate was evaporated in vacuo. The resulting residue was purified using column chromatography (eluted with 0-20% EtOAc/DCM) to provide (E)-2,6-dichloro-3-(2-ethoxyvinyl)pyridine (1.96 mg, yield: 86%). MS (M+H)+: 218.

Fuente