Reacción #68645

Ecuación de reacción

8-chloro-1,5-naphthyridin-3-ol

cesium carbonate

2,2,2-trifluoroethyl trifluoromethanesulfonate

→

8-chloro-3-(2,2,2-trifluoroethoxy)-1,5-naphthyridine

Rendimiento 56.3%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroVessel sealed
2. 2
   OtroReaction
3. 3
   OtroQuench with water
4. 4
   workup.ADDITIONdilute with aqueous sodium bicarbonate solution and dichloromethane
5. 5
   OtroLayers separated
6. 6
   Otroorganic layer collected
7. 7
   Secadodried over sodium sulfate
8. 8
   ConcentraciónThis was concentrated
9. 9
   Otroto afford yellow oil
10. 10
    Otrowhich was purified by ISCO silica gel chromatography (20-40% EtOAc/Hexanes)

Procedimiento

A resealable pressure bottle was charged with 8-chloro-1,5-naphthyridin-3-ol (80 mg, 0.44 mmol), cesium carbonate (433 mg, 1.3 mmol), 2,2,2-trifluoroethyl trifluoromethanesulfonate (360 mg, 1.55 mmol), and DMF (0.9 ml). Vessel sealed and placed in a pre-heated at 50° C. oil bath. Reaction allowed to stir at this temperature for 45 minutes. LC/MS shows complete conversion. Quench with water, dilute with aqueous sodium bicarbonate solution and dichloromethane. Layers separated, organic layer collected and dried over sodium sulfate. This was concentrated to afford yellow oil; which was purified by ISCO silica gel chromatography (20-40% EtOAc/Hexanes) to afford 8-chloro-3-(2,2,2-trifluoroethoxy)-1,5-naphthyridine (65 mg, 56% yield). MS [M+H]=263.0@1.89 minutes. Calc'd for C10H6ClF3N2O=262.6.

Fuente