反应详情

A stirred suspension of 4-bromonaphth-1-ylamine (10 g, 45 mnmole) in 1,2-dimethoxyethane (400 ml) and water (100 ml) containing sodium carbonate (14 g) was flushed with argon for 0.3h. Tetrakis (triphenylphosphine)palladium (0) (2.75 g, 2.4 mmole) was added followed by 4-pyridylboronic acid (5.7 g, 46 mmole) and the mixture heated at reflux for 5 h. The mixture was concentrated in vacuo to a brown slurry and partitioned between dichloromethane and water. The aqueous was further extracted with dichloromethane and the combined organics dried (Na2SO4) and concentrated in vacuo to a brown solid (13.2 g). Purification of the solid by flash chromatography eluting with ethyl acetate afforded the title compound as a yellow crystalline solid (7.8 g, 78%).

1. customwas flushed with argon for 0.3h
2. temperaturethe mixture heated
3. temperatureat reflux for 5 h
4. concentrationThe mixture was concentrated in vacuo to a brown slurry
5. custompartitioned between dichloromethane and water
6. extractionThe aqueous was further extracted with dichloromethane
7. dry with materialthe combined organics dried (Na2SO4)
8. concentrationconcentrated in vacuo to a brown solid (13.2 g)
9. customPurification of the solid by flash chromatography
10. washeluting with ethyl acetate