Potassium Carbonate → HCID 59306790, compound

HRID 1052922Notes

Reaction equation

HRID 1052922 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]3C=C(B4OC(C)(C)C(C)(C)O4)C=C[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.COCCOC>[C:15]1([N:21]2[C:22]3[CH:23]=[C:24]([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:25]=[CH:26][C:27]=3[C:28]3[C:33]2=[CH:3][CH:2]=[CH:14][CH:13]=3)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2524463-BromocarbazoleHCID 598587389- Phenyl-2-(4,4,5,5-tetraMethyl- 1,3,2-dioxaborolan-2-yl)-9H-carbazole

Product 1

HCID 59306790HCID 59306790, compoundYield 156.6%

Reagents, catalysts & solvents 3

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

Procedure

Next, a mixed solution of 4.0 g of 3-bromocarbazole, 6.6 g of 9-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole, 18 ml of a 2M aqueous potassium carbonate solution, 80 ml of 1,2-dimethoxyethane, 72 mg of palladium acetate and 243 mg of tris(2-methylphenyl)phosphine was refluxed for 6 hours under a nitrogen flow. The solution was cooled to room temperature, and then extracted with toluene. The organic layer was washed with 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 5.2 g of 9-phenyl-9H,9′H-2,3′-bicarbazole.

Workup

  1. extractionextracted with toluene
  2. washThe organic layer was washed with 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-aedd0a95f7814e328937bb8ee0dd8f88
Source dataset
uspto-grants-2016_07
Patent number
US09391288B2

Reaction notes

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