Carbazole → 9-(pyridin-2-yl)-9H-carbazole

HRID 716595Notes

Reaction equation

HRID 716595 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=C(C3C(OC)=CC=CC=3OC)C=CC=2)CCCCC1>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2

Participants

7

Reactant 3

HCID 6854CarbazoleHCID 79732-BromopyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 101017639-(pyridin-2-yl)-9H-carbazoleYield 83%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 58401078Dicyclohexyl(2',6'-dimethoxybiphenyl-3-yl)phosphineCatalystHCID 1140TolueneSolvent

Procedure

9-H-carbazole (20 g, 120 mmol), and 2-bromopyridine (13 mL, 132 mmol) were mixed in dry toluene (500 mL). The solution was bubbled nitrogen while stirring for 15 min. Pd2(dba)3 (0.6 g, 0.66 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-3-yl)phosphine (1 g, 0.24 mmol) and sodium tert-butoxide (20 g, 200 mmol) were added in sequence. The mixture was heated to reflux overnight under nitrogen. After cooling, the reaction mixture was filtered through Celite®/silica pad and the solvent was then evaporated. The residue was then purified by silica gel column chromatography using toluene:hexane (1:1, v/v) as eluent to obtain 24.3 g (83%) of the desired product.

Workup

  1. customThe solution was bubbled nitrogen
  2. temperatureThe mixture was heated
  3. temperatureto reflux overnight under nitrogen
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture was filtered through Celite®/silica pad
  6. customthe solvent was then evaporated
  7. customThe residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e345933cea7f41158abcb3b2a159293b
Source dataset
uspto-grants-2015_11
Patent number
US09190623B2

Reaction notes

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