Reaktion #74664

Reaktionsgleichung

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

Lösungsmittel

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas sparged 5 minutes with argon
2. 2
   Sonstigethe reaction vial was capped
3. 3
   Temperaturthe reaction mixture was cooled to ambient temperature
4. 4
   ExtraktionThe mixture was extracted with ethyl acetate (3×)
5. 5
   WaschenThe combined organic layers were washed with brine
6. 6
   Trocknendried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   Einengenconcentrated onto diatomaceous earth
10. 10
    Sonstigepurified by automated flash chromatography (24 g SiO2, hexanes to 3:1 hexanes-ethyl acetate)

Vorschrift

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.

Quelle