Carbazole → HCID 68267060, compound

HRID 1753713Notes

Reaction equation

HRID 1753713 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]2[S:6][C:7]3[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[CH:16]1[C:28]2[NH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1.CC(C)([O-])C.[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.C1(C)C=CC=CC=1>[Br:13][C:10]1[CH:11]=[CH:12][C:7]2[S:6][C:5]3[CH:14]=[CH:15][C:2]([N:27]4[C:28]5[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=5[C:21]5[C:26]4=[CH:25][CH:24]=[CH:23][CH:22]=5)=[CH:3][C:4]=3[C:8]=2[CH:9]=1

Participants

7

Reactant 3

HCID 6854CarbazoleHCID 6311202,8-DibromodibenzothiopheneHCID 23676156Sodium t-butoxide

Product 1

HCID 68267060HCID 68267060, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 27342162-(Dicyclohexylphosphino)biphenylCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 29.1 g (85.2 mmole) 2,8-dibromodibenzo[b,d]thiophene, 14.2 g (85.2 mmole) of carbazole, 0.12 g (0.54 mmole) of palladium(II) acetate, 0.4 g (1.14 mmol) of 2-(dicyclohexylphosphino)biphenyl, 10 g (104 mmole) sodium tert-butoxide and 300 ml toluene were refluxed under nitrogen for about overnight, then cooled to room temperature, the organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica(hexane-dichloromethane) to give product 18.6 g (51%).

Workup

  1. temperaturewere refluxed under nitrogen for about overnight
  2. extractionthe organic layer was extracted with ethyl acetate and water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customthe solvent was removed
  5. customthe residue was purified by column chromatography on silica(hexane-dichloromethane)

Sources & evidence

ORD record
ord-e8ff3abde22249468bdb3b98d4c635a9
Source dataset
uspto-grants-2015_10
Patent number
US09166177B2

Reaction notes

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