Reacción #68649

Ecuación de reacción

sodium bicarbonate

7-bromo-1,5-naphthyridin-4(1H)-one

DMF

Oxalyl chloride

→

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

Rendimiento 14.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroset up with a reflux condenser
2. 2
   OtroArgon bubbled through
3. 3
   OtroReaction mixture
4. 4
   Otroreaction
5. 5
   OtroReaction mixture
6. 6
   ExtracciónProduct extracted with DCM (500 mL) three times
7. 7
   Secadodried over sodium sulfate
8. 8
   Concentraciónconcentrated
9. 9
   Otroto afford brown solid
10. 10
    OtroThis was purified by ISCO silica gel chromatography

Procedimiento

7-bromo-1,5-naphthyridin-4(1H)-one (23.8 g, 105.8 mmol), acetonitriel (192 mL, 105.8 mmol), and DMF (2.05 mL, 26.5 mmol) were placed in a 3-necked round bottom flask set up with a reflux condenser. Argon bubbled through. Reaction mixture brought to reflux (˜95° C.). Oxalyl chloride (28.7 ml, 328.1 mmol) was added dropwise via addition funnel over 40 minutes and reaction allowed to stir at this temperature for 16 hrs. Reaction mixture cooled to 0° C. and basified to pH ˜8 with aqueous sodium bicarbonate solution. Product extracted with DCM (500 mL) three times. Organic layers combined, dried over sodium sulfate and concentrated to afford brown solid. This was purified by ISCO silica gel chromatography to afford 3-bromo-8-chloro-1,5-naphthyridine (3.6 g, 14% yield) as fluffy tan solid.

Fuente