Reacción #1869193

Ecuación de reacción

bromopyridine

6-Bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one

trans-2-phenylvinylboronic acid

potassium carbonate

→

solid

Rendimiento 38.0%

6-((E)-Styryl)-4H-pyrido[3,2-b][1,4]oxazin-3-one

Rendimiento 38.0%

Disolventes

EtOAc

1,4-dioxane

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solution was degassed with argon
2. 2
   TemperaturaThe reaction was heated
3. 3
   Temperaturaat reflux under argon overnight
4. 4
   LavadoThe solution was washed sequentially with water and brine
5. 5
   Secadodried (Na2SO4)
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3)

Procedimiento

The bromopyridine (h) (6.0 g, 26.3 mmol) and trans-2-phenylvinylboronic acid (3.9 g, 26.3 mmol) were dissolved in 1,4-dioxane (150 ml) and the solution was degassed with argon. (Ph3P)4Pd (230 mg, 0.2 mmol) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmol) in water (20 ml). The reaction was heated at reflux under argon overnight, then was cooled to room temperature and diluted with EtOAc (200 ml). The solution was washed sequentially with water and brine, dried (Na2SO4), and concentrated in vacuo. The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3) to afford a solid (2.5 g, 38%).

Fuente