Reacción #88662

Ecuación de reacción

3-(5-bromo-2-furyl)acryloyl azide

diphenyl ether

tributylamine

→

title compound

2-Bromofuro[3,2-c]pyridin-4(5H)-one

Disolventes

tert-butyl methyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato cool to room temperature
2. 2
   FiltraciónThe resulting solid was collected by filtration
3. 3
   OtroThe obtained solid was purified by silica gel column chromatography (hexane
4. 4
   workup.ADDITIONTo the obtained fraction was added a saturated aqueous sodium hydrogen carbonate solution
5. 5
   Extracciónthe mixture was extracted with ethyl acetate
6. 6
   SecadoThe extract was dried over anhydrous magnesium sulfate
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   Otrorecrystallized from ethyl acetate

Procedimiento

A mixture of 3-(5-bromo-2-furyl)acryloyl azide (20.7 g), diphenyl ether (200 mL) and tributylamine (16 mL) was stirred at 220-230° C. for 30 min under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature, and tert-butyl methyl ether (200 mL) was added thereto. The resulting solid was collected by filtration. The obtained solid was purified by silica gel column chromatography (hexane, then ethyl acetate/THF), followed by HPLC (C18, mobile phase: water/acetonitrile (including 0.1% TFA)). To the obtained fraction was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, concentrated in vacuo, and recrystallized from ethyl acetate to give the title compound (7.00 g) as a white solid.

Fuente