Reaction #2126613

Reaction equation

9-(9H-carbazol-3-yl)-pyrido[2,3-b]indole

4-(3′-bromo-[1,1′-biphenyl]-3-yl)dibenzo[b,d]thiophene

sodium tert-butoxide

→

9-(9-(3′-(dibenzo[b,d]thiophen-4-yl)-[1,1′-biphenyl]-3-yl)-carbazol-3-yl)-pyrido[2,3-b]indole

Yield 64.1%

Solvents

xylene

Conditions

Workup

1. 1
   Washthe reaction mixture was washed with water
2. 2
   Dryingdried over Na2SO4
3. 3
   Otherthe solvent was evaporated
4. 4
   workup.DISSOLUTIONThe residue was dissolved in hot toluene
5. 5
   workup.ADDITIONmixed with celite
6. 6
   Otherpurified by column chromatography with hexane:toluene (1:9 to 0:10
7. 7
   OtherThe product was precipitated in ethanol
8. 8
   Otherfurther purified by thermal sublimation under vacuum (<105 torr)

Procedure

A solution of 9-(9H-carbazol-3-yl)-pyrido[2,3-b]indole (2.50 g, 7.50 mmol), 4-(3′-bromo-[1,1′-biphenyl]-3-yl)dibenzo[b,d]thiophene (3.11 g, 7.50 mmol), Pd2(dba)3 (0.137 g, 0.150 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-3-yl)phosphine (0.123 g, 0.30 mmol), and sodium tert-butoxide (1.44 g, 15.00 mmol) in xylene (150 mL) was refluxed in nitrogen overnight. After cooling to room temperature, the reaction mixture was washed with water, dried over Na2SO4 and the solvent was evaporated. The residue was dissolved in hot toluene, mixed with celite, and purified by column chromatography with hexane:toluene (1:9 to 0:10, v/v) as eluent. The product was precipitated in ethanol, and further purified by thermal sublimation under vacuum (<105 torr) to yield 9-(9-(3′-(dibenzo[b,d]thiophen-4-yl)-[1,1′-biphenyl]-3-yl)-carbazol-3-yl)-pyrido[2,3-b]indole as a white glassy solid (3.21 g).

Source