反应详情

Phenylboronic acid (11.0 g, 90 mmol), 2-chloro-4-ethyl-5-iodopyridine (8.00 g, 30 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (492 mg, 1.2 mmol), and potassium phosphate tribasic (20.7 g, 90 mmol), 250 ml, of toluene and 25 mL of water were placed in a 1 L round-bottom flask. Nitrogen was bubbled directly into the mixture for 30 min after which tris(dibenzylideneacetone)dipalladium(0) (275 mg, 0.3 mmol) was added. Nitrogen was bubbled for another 15 min, then the reaction mixture was heated to reflux for 16 h under nitrogen. After the reaction was completed the mixture was cooled and the organic layer was separated from the aqueous layer. The organic layer was washed with saturated brine solution and dried over magnesium sulfate. The solution was filtered and the solvent was removed under vacuum to give a off-white solid. This crude was purified by silica gel column chromatography eluting with 10% ethyl acetate/hexanes. 7.0 g of desired product was obtained after purification (90.9% yield).

1. additionwas added
2. customNitrogen was bubbled for another 15 min
3. temperaturethe reaction mixture was heated
4. temperatureto reflux for 16 h under nitrogen
5. temperaturewas cooled
6. customthe organic layer was separated from the aqueous layer
7. washThe organic layer was washed with saturated brine solution
8. dry with materialdried over magnesium sulfate
9. filtrationThe solution was filtered
10. customthe solvent was removed under vacuum
11. customto give a off-white solid
12. customThis crude was purified by silica gel column chromatography
13. washeluting with 10% ethyl acetate/hexanes