Reaktion #86547

Reaktionsgleichung

sodium carbonate

water

7-(1-azidoethyl)-6-bromo-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

(3,5-difluorophenyl)boronic acid

→

desired product

Ausbeute 53.0%

7-(1-azidoethyl)-6-(3,5-difluorophenyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Ausbeute 53.0%

Lösungsmittel

1,4-dioxane

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Waschenwashed with water and brine
3. 3
   Trocknendried over MgSO4
4. 4
   Einengenconcentrated
5. 5
   Sonstigepurified on silica gel (0-45% ethyl acetate/hexanes)

Vorschrift

To a mixture of 7-(1-azidoethyl)-6-bromo-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (0.50 g, 1.7 mmol) and (3,5-difluorophenyl)boronic acid (0.31 g, 2.0 mmol) in 1,4-dioxane (10 mL) was added a 1 N solution of sodium carbonate in water (2.2 mL, 2.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.096 g, 0.083 mmol). The mixture was stirred at 100° C. overnight. After cooling, the mixture was diluted with ethyl acetate, washed with water and brine, dried over MgSO4, concentrated, and purified on silica gel (0-45% ethyl acetate/hexanes) to give the desired product (0.30 g, 53%). LCMS calculated for C14H10F2N5OS (M+H)+: m/z=334.1. Found: 334.0.

Quelle