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

HRID 1052923Notes

Reaction equation

HRID 1052923 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.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(COC)OC>[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

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2524463-BromocarbazoleHCID 513584509-Phenyl-9H-carbazole-3-boronic acid

Product 1

HCID 593066299-Phenyl-9H,9'H-[3,3']bicarbazolylYield 63.3%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixed solution of 20.9 g of 3-bromocarbazole, 15.0 g of 9-phenylcarbazole-3-boronic acid, 366 mg of palladium acetate, 300 mg of tris(2-methylphenyl)phosphine, 105 ml of a 2M aqueous potassium carbonate solution and 260 ml of dimethoxyethane was refluxed for 6 hours under a nitrogen flow. The solution was cooled to room temperature, and then extracted with 500 ml of tetrahydrofuran. The organic layer was washed with 100 ml of a saturated saline solution twice, dried over magnesium sulfate, and then evaporated. The resultant concentrate was purified by o-xylene recrystallization and then vacuum-dried to obtain 13.5 g of 9-phenyl-9H,9′H-3,3′-bicarbazole.

Workup

  1. extractionextracted with 500 ml of tetrahydrofuran
  2. washThe organic layer was washed with 100 ml of a saturated saline solution twice
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. concentrationThe resultant concentrate
  6. customwas purified by o-xylene recrystallization
  7. customvacuum-dried

Sources & evidence

ORD record
ord-f963bd16cdc64d679f99b4ee8c3edda1
Source dataset
uspto-grants-2016_07
Patent number
US09391288B2

Reaction notes

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