Carbazole → HCID 59561713, compound

HRID 2172413Notes

Reaction equation

HRID 2172413 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[CH:30]1[C:42]2[NH:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]=2[CH:33]=[CH:32][CH:31]=1.Br[C:44]1[CH:61]=[CH:60][C:59]2[C:58]3[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=3)[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46]=2[CH:45]=1.CC(C)([O-])C.[Na+]>CC1C=CC=CC=1C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:45]1[C:46]2[C:47]3[C:52](=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:53]3[C:58](=[CH:57][CH:56]=[CH:55][CH:54]=3)[C:59]=2[CH:60]=[CH:61][C:44]=1[N:41]1[C:40]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:34]2[C:42]1=[CH:30][CH:31]=[CH:32][CH:33]=2

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 183811742-BromotriphenyleneHCID 23676156Sodium t-butoxide

Product 1

HCID 59561713HCID 59561713, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 7237O-XyleneSolvent

Procedure

To a stirred solution of Pd2(dba)3 (0.52 g, 0.57 mmol) in o-xylene (140 mL), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.94 g, 2.3 mmol) was added and degassed with nitrogen for 15 minutes. Carbazole (5.33 g, 31.9 mmol) and 2-bromotriphenylene (7.0 g, 22.7 mmol), sodium tert-butoxide (6.57 g, 68.3 mmol) were added and degassed with nitrogen for another 15 minutes. The reaction was refluxed for 2 days. The reaction mixture was filtered through silica, washed with DCM and dried under vacuum. Silica gel chromatography with 10% DCM/hexane, yielded 4.98 g of a while solid (56%) as the product.

Workup

  1. customdegassed with nitrogen for 15 minutes
  2. customdegassed with nitrogen for another 15 minutes
  3. temperatureThe reaction was refluxed for 2 days
  4. filtrationThe reaction mixture was filtered through silica
  5. washwashed with DCM
  6. customdried under vacuum

Sources & evidence

ORD record
ord-2e1cd416c0ab4d17a94112abfd25c2c1
Source dataset
uspto-grants-2015_06
Patent number
US09054323B2

Reaction notes

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