Dichloromethane → HCID 69640157, compound

Participants

Reaction Steps

A mixture of 10.00 g of acridan (55.2 mmol), 247.7 mg of Pd(OAc)2 (1.10 mmol), 178.6 mg of tri-t-butylphosphine (0.88 mmol), 7.95 g of sodium t-butoxide (82.7 mmol), and 6.3 mL of 2-bromopyridine (66.2 mmol) in 100 mL of dry toluene was allowed to stir under inert atmosphere for 18 h. The reaction mixture was poured into a mixture of 300 mL of CH2Cl2 and 100 g of silica gel with stirring. The mixture was filtered, and the solid material was washed with 1 L of CH2Cl2. The filtrate was concentrated in vacuo to afford a yellow oil, which was taken up in hexanes. The semi-solution was again concentrated in vacuo to afford a yellow solid. The solid was triturated in 100 mL of hexanes for several hours, filtered and dried to afford 12.50 g of N-pyridylacridan (88%).

Provenance & Evidence