Reacción #74664

Ecuación de reacción

4-chloro-2-iodo-1-methoxybenzene

(2-chloropyridin-4-yl)boronic acid

sodium carbonate

1,4-dioxane

→

product

2-Chloro-4-(5-chloro-2-methoxyphenyl)pyridine

Disolventes

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas sparged 5 minutes with argon
2. 2
   Otrothe reaction vial was capped
3. 3
   Temperaturathe reaction mixture was cooled to ambient temperature
4. 4
   ExtracciónThe mixture was extracted with ethyl acetate (3×)
5. 5
   LavadoThe combined organic layers were washed with brine
6. 6
   Secadodried over sodium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   Concentraciónconcentrated onto diatomaceous earth
10. 10
    Otropurified by automated flash chromatography (24 g SiO2, hexanes to 3:1 hexanes-ethyl acetate)

Procedimiento

A mixture of 4-chloro-2-iodo-1-methoxybenzene (542 mg, 2.02 mmol), (2-chloropyridin-4-yl)boronic acid (400 mg, 2 mmol), and sodium carbonate (860.2 mg, 8.116 mmol) in 1,4-dioxane (8.4 mL, 110 mmol) and water (2.8 mL, 160 mmol) was sparged 5 minutes with argon. Tetrakis(triphenylphosphine)palladium(0) (139.9 mg, 0.1210 mmol) was added and the reaction vial was capped. The reaction mixture was heated at 90° C. After 3 hours, the reaction mixture was cooled to ambient temperature and poured into water. The mixture was extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was taken up in methylene chloride, concentrated onto diatomaceous earth, and purified by automated flash chromatography (24 g SiO2, hexanes to 3:1 hexanes-ethyl acetate) to afford the product as a light yellow powder.

Fuente