반응 #1869193

반응 방정식

bromopyridine

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

trans-2-phenylvinylboronic acid

potassium carbonate

→

solid

수율 38.0%

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

수율 38.0%

용매

EtOAc

1,4-dioxane

water

반응 조건

후처리

1. 1
   기타the solution was degassed with argon
2. 2
   온도The reaction was heated
3. 3
   온도at reflux under argon overnight
4. 4
   세척The solution was washed sequentially with water and brine
5. 5
   건조dried (Na2SO4)
6. 6
   농축concentrated in vacuo
7. 7
   기타The solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3)

실험 절차

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%).

출처