Reacción #166649

Ecuación de reacción

3-iodo-1-((6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole

1,10-phenanthroline

potassium fluoride

methanol

→

3-methoxy-1-((6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole

Rendimiento 66.0%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas purged with argon
2. 2
   Temperaturaheated
3. 3
   Temperaturaat reflux for 14 hours
4. 4
   TemperaturaAfter cooling
5. 5
   Filtraciónthe mixture was filtered through glass fiber
6. 6
   Filtraciónfilter paper
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   Otropurified by silica gel chromatography (5-25% EtOAc in hexanes)

Procedimiento

A mixture of 3-iodo-1-((6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole (0.520 g, 1.32 mmol), 1,10-phenanthroline (0.238 g, 1.32 mmol), copper iodide (0.251 g, 1.32 mmol) and potassium fluoride (40% on alumina) (1.05 g, 7.26 mmol) in methanol (2.7 mL) and toluene (13 mL) was purged with argon and heated at reflux for 14 hours. After cooling, the mixture was filtered through glass fiber filter paper, concentrated under reduced pressure and purified by silica gel chromatography (5-25% EtOAc in hexanes) to give 3-methoxy-1-((6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole (0.260 g, 66% yield) as a brown gum.

Fuente