反应详情

A stirred suspension of 4-bromonaphth-1-ylamine (10 g, 45 mmole) in 1,2-dimethoxyethane (400 ml) and water (100 ml) containing sodium carbonate (14 g) was flushed with argon for 0.3 hours. Tetrakis(triphenylphosphine) palladium (0) (2.75 g, 2.4 mmole) was added followed by pyridin-4-ylboronic acid (5.7 g, 46 mmole) and the mixture heated at reflux for 5 hours. 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 0.3 hours
2. temperaturethe mixture heated
3. temperatureat reflux for 5 hours
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