Reacción #331765

Ecuación de reacción

diisopropyl azodicarboxylate

3-bromo-5-hydroxypyridine

benzyl alcohol

triphenylphosphine

→

title compound

Rendimiento 31.9%

3-Benzyloxy-5-bromo-pyridine

Rendimiento 31.9%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction mixture is concentrated in vacuo
2. 2
   workup.ADDITIONThe residue is diluted with EtOAc
3. 3
   Lavadowashed
4. 4
   Otrodried under anhy
5. 5
   FiltraciónNa2SO4, filtered
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe residue is purified by flash chromatography (SiO2, 0-5% MeOH/CH2Cl2)

Procedimiento

To a vial is added 3-bromo-5-hydroxypyridine (200 mg, 1.15 mmol), benzyl alcohol (137 mg, 1.27 mmol) and triphenylphosphine (332 mg, 1.27 mmol) in THF (5 ml) at 0° C., followed by the addition of diisopropyl azodicarboxylate (256 mg, 1.27 mmol). The reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is concentrated in vacuo. The residue is diluted with EtOAc, washed with sat NaHCO3, water, brine, dried under anhy. Na2SO4, filtered and concentrated. The residue is purified by flash chromatography (SiO2, 0-5% MeOH/CH2Cl2) to afford title compound (97 mg); m/z 264.0, 266.0 [M, M+2H]

Fuente