Sodium Carbonate → 4-(Pyridin-4-yl)naphth-1-ylamine

Beteiligte Stoffe

Reaktionsschritte

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%).

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