Reaktion #68647

Reaktionsgleichung

sodium 2-chloro-2,2-difluoroacetate

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

cesium carbonate

DMF

→

8-chloro-3-(difluoromethoxy)-1,5-naphthyridine

Ausbeute 56.0%

Lösungsmittel

Methanol Dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThis was then placed in a 100° C.
2. 2
   SonstigeReaction mixture
3. 3
   Filtrationfiltered over celite
4. 4
   EinengenFiltrate concentrated
5. 5
   Sonstigepurified by ISCO silica gel chromatography (40 g) in 1% MeOH/DCM

Vorschrift

A round bottom flask under nitrogen atmosphere was charged with sodium 2-chloro-2,2-difluoroacetate (0.49 g, 3.2 mmol), 8-chloro-1,5-naphthyridin-3-ol (0.25 g, 1.4 mmol), cesium carbonate (1.4 g, 4.2 mmol), and DMF (2.8 mL, 0.5M). This was then placed in a 100° C. preheated oil bath and stirred at this temperature for 3 hours. Reaction mixture diluted with 10% Methanol/Dichloromethane and filtered over celite. Filtrate concentrated and purified by ISCO silica gel chromatography (40 g) in 1% MeOH/DCM to afford pure 8-chloro-3-(difluoromethoxy)-1,5-naphthyridine (0.18 g, 56% yield) as white solid. MS [M+H]=231.2. Calc'd for C9H5ClF2N2O=230.60.

Quelle