Reaction #1509637

Reaction equation

Compound 10

1-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazole

9-(4-bromophenyl)-9H-carbazole

KF

ethyl acetate

→

Compound 11

Yield 47.0%

9-(4′-(1-phenyl-1H-benzo[d]imidazol-2-yl)biphenyl-4-yl)-9H-carbazole

Yield 47.0%

Solvents

DMF

Conditions

Workup

1. 1
   TemperatureAfter cooling to r.t.
2. 2
   FiltrationThe resulting mixture was filtered
3. 3
   OtherThe solid was collected
4. 4
   workup.DISSOLUTIONdissolved in DCM (200 mL)
5. 5
   Filtrationwhich was filtered
6. 6
   Concentrationconcentrated
7. 7
   Otherrecrystallized

Procedure

A mixture of Compound 10 (1.41 g, 3.56 mmol), 9-(4-bromophenyl)-9H-carbazole (1.15 g, 3.56 mmol), Pd(dppf)Cl2 (100 mg, 0.14 mmol) and KF (0.619 g, 10.7 mmol) in anhydrous DMF (20 mL) was heated at 120° C. under argon overnight. After cooling to r.t., ethyl acetate (200 mL) was added and the whole was stirred for 15 min. The resulting mixture was filtered. The solid was collected and dissolved in DCM (200 mL), which was filtered, concentrated and recrystallized to give a white solid (Compound 11) (550 mg).

Source