Reaction #803777

Reaction equation

9-H-carbazole

2-bromopyridine

sodium tert-butoxide

→

desired product

Yield 83.0%

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

Yield 83.0%

Solvents

toluene

Conditions

Workup

1. 1
   OtherThe solution was bubbled nitrogen
2. 2
   TemperatureThe mixture was heated
3. 3
   Temperatureto reflux overnight under nitrogen
4. 4
   TemperatureAfter cooling
5. 5
   Filtrationthe reaction mixture was filtered through Celite®/silica pad
6. 6
   Otherthe solvent was then evaporated
7. 7
   OtherThe residue was then purified by silica gel column chromatography

Procedure

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.

Source