Potassium Carbonate → 9-Phenyl-9H,9'H-[3,3']bicarbazolyl

HRID 1184049Notes

Reaction equation

HRID 1184049 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[C:15]1([N:21]2[C:33]3[CH:32]=[CH:31][C:30](B([O-])[O-])=[CH:29][C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.COC(OC)(O)C.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:15]1([N:21]2[C:33]3[CH:32]=[CH:31][C:30]([C:2]4[CH:3]=[CH:4][C:5]5[NH:6][C:7]6[C:12]([C:13]=5[CH:14]=4)=[CH:11][CH:10]=[CH:9][CH:8]=6)=[CH:29][C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 2524463-BromocarbazoleHCID 184133611,1-Dimethoxyethan-1-olHCID 86629095N-phenylcarbazole-3-boronate

Product 1

HCID 593066299-Phenyl-9H,9'H-[3,3']bicarbazolylYield 80%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×

Procedure

2.5 g (10 mmol) of 3-bromocarbazole, 2.9 g (10 mmol) of N-phenylcarbazole-3-boronate, and 152 mg (0.50 mmol) of tri(ortho-tolyl)phosphine were put into a 200 mL three-neck flask. The atmosphere in the flask was substituted with nitrogen. 50 mL of dimethoxyethanol (DME) and 10 mL of potassium carbonate solution (2 mol/L) were added to the mixture. The mixture was stirred while pressure is reduced so as to be deaerated. After the deaeration, 50 mg (0.2 mmol) of palladium acetate was added. The mixture was stirred at 80° C. for three hours under a nitrogen stream. After the stir, about 50 mL of toluene was added to the mixture and the mixture was stirred for about 30 minutes, and then the mixture was washed with water and saturated saline in this order. After the washing, an organic layer was dried with magnesium sulfate. The mixture was naturally filtrated, and the obtained filtrate was concentrated, so that an oily substance was obtained. The obtained oily substance was dissolved in toluene, the solution was filtrated through Florisil, alumina, and celite, and the obtained filtrate was concentrated, so that 3.3 g of a white solid substance, which was the object, was obtained in a yield of 80%. The synthesis scheme of Step 1 is shown in the following (B-1).

Workup

  1. stirringThe mixture was stirred at 80° C. for three hours under a nitrogen stream
  2. stirringthe mixture was stirred for about 30 minutes
  3. washthe mixture was washed with water and saturated saline in this order
  4. dry with materialAfter the washing, an organic layer was dried with magnesium sulfate
  5. filtrationThe mixture was naturally filtrated
  6. concentrationthe obtained filtrate was concentrated, so that an oily substance
  7. customwas obtained
  8. filtrationthe solution was filtrated through Florisil, alumina, and celite
  9. concentrationthe obtained filtrate was concentrated, so that 3.3 g of a white solid substance, which
  10. customwas obtained in a yield of 80%
  11. customThe synthesis scheme of Step 1

Sources & evidence

ORD record
ord-cb79a9df6dd74ec08ac7f0d8bb2c6b33
Source dataset
uspto-grants-2014_03
Patent number
US08664849B2

Reaction notes

Loading…