反応 #1869193

反応方程式

bromopyridine

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

trans-2-phenylvinylboronic acid

potassium carbonate

→

solid

収率 38.0%

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

収率 38.0%

溶媒

EtOAc

1,4-dioxane

water

反応条件

後処理

1. 1
   その他the solution was degassed with argon
2. 2
   温度The reaction was heated
3. 3
   温度at reflux under argon overnight
4. 4
   洗浄The solution was washed sequentially with water and brine
5. 5
   乾燥dried (Na2SO4)
6. 6
   濃縮concentrated in vacuo
7. 7
   その他The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3)

実験手順

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%).

出典