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

HRID 1052918Notes

Reaction equation

HRID 1052918 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.C1([C:21]2[C:33]3[NH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25]=3[CH:24]=[C:23](B(O)O)[CH:22]=2)C=CC=CC=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:2]1([N:6]2[C:5]3[CH:4]=[CH:3][C:2]([C:23]4[CH:22]=[CH:21][C:33]5[NH:32][C:31]6[C:26]([C:25]=5[CH:24]=4)=[CH:27][CH:28]=[CH:29][CH:30]=6)=[CH:14][C:13]=3[C:12]3[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:3]=[CH:4][CH:5]=[CH:13][CH:14]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2524463-BromocarbazoleHCID 86706009HCID 86706009, compound

Product 1

HCID 593066299-Phenyl-9H,9'H-[3,3']bicarbazolylYield 77.8%

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 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 toluene. The organic layer was washed with 100 ml of water twice, dried over magnesium sulfate, and then evaporated. The resultant concentrate was purified by silica gel column chromatography 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 toluene
  2. washThe organic layer was washed with 100 ml of water twice
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. concentrationThe resultant concentrate
  6. customwas purified by silica gel column chromatography
  7. customvacuum-dried

Sources & evidence

ORD record
ord-ee20eedad76544c287c2435956186bad
Source dataset
uspto-grants-2016_07
Patent number
US09391288B2

Reaction notes

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