تفاعل #74664

معادلة التفاعل

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

المذيبات

water

water

ظروف التفاعل

المعالجة

1. 1
   أخرىwas sparged 5 minutes with argon
2. 2
   أخرىthe reaction vial was capped
3. 3
   درجة الحرارةthe reaction mixture was cooled to ambient temperature
4. 4
   استخلاصThe mixture was extracted with ethyl acetate (3×)
5. 5
   غسيلThe combined organic layers were washed with brine
6. 6
   تجفيفdried over sodium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated in vacuo
9. 9
   تركيزconcentrated onto diatomaceous earth
10. 10
    أخرىpurified by automated flash chromatography (24 g SiO2, hexanes to 3:1 hexanes-ethyl acetate)

الإجراء التجريبي

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.

المصدر