Reaktion #1869193

Reaktionsgleichung

bromopyridine

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

trans-2-phenylvinylboronic acid

potassium carbonate

→

solid

Ausbeute 38.0%

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

Ausbeute 38.0%

Lösungsmittel

EtOAc

1,4-dioxane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solution was degassed with argon
2. 2
   TemperaturThe reaction was heated
3. 3
   Temperaturat reflux under argon overnight
4. 4
   WaschenThe solution was washed sequentially with water and brine
5. 5
   Trocknendried (Na2SO4)
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe solid residue was purified by flash chromatography on silica gel (5-10% EtOAc/CHCl3)

Vorschrift

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%).

Quelle