Reacción #68643

Ecuación de reacción

8-chloro-3-methoxy-1,5-naphthyridine

boron tribromide

dichloroethane

→

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

Rendimiento 56.2%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroVessel sealed
2. 2
   TemperaturaNext day the reaction mixture was chilled in ice bath
3. 3
   FiltraciónThe resulting yellow solid material was then filtered
4. 4
   Otrodried under high vacuum
5. 5
   Otropurified in this system by ISCO silica gel chromatography (80 g)

Procedimiento

A pressure-resistant vial was charged with 8-chloro-3-methoxy-1,5-naphthyridine (2.5 g, 12.8 mmol), boron tribromide (13.4 mL, 141.3 mmol) and dichloroethane (0.6M, 21.4 mL). Vessel sealed and mixture stirred at 60° C. for 16 hrs. Next day the reaction mixture was chilled in ice bath and diluted with dichloromethane (200 mL). This was allowed to sit under nitrogen system until all fuming ceased. The resulting yellow solid material was then filtered and dried under high vacuum. This was suspended in 40% (90:10:1 DCM/MeOH/NH4OH)/DCM and purified in this system by ISCO silica gel chromatography (80 g) afford 8-chloro-1,5-naphthyridin-3-ol (1.3 g, 56% yield). MS [M+H]=181.2. Calc'd for C8H5ClN2O=180.59.

Fuente