Carbazole → 9-(pyridin-2-yl)-9H-carbazole

Participants

Reaction Steps

9-H-carbazole (20 g, 120 mmol), and 2-bromopyridine (13 mL, 132 mmol) were mixed in dry toluene (500 mL). The solution was bubbled nitrogen while stirring for 15 min. Pd2(dba)3 (0.6 g, 0.66 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-3-yl)phosphine (1 g, 0.24 mmol) and sodium tert-butoxide (20 g, 200 mmol) were added in sequence. The mixture was heated to reflux overnight under nitrogen. After cooling, the reaction mixture was filtered through Celite®/silica pad and the solvent was then evaporated. The residue was then purified by silica gel column chromatography using toluene:hexane (1:1, v/v) as eluent to obtain 24.3 g (83%) of the desired product.

Provenance & Evidence