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

HRID 890833Notes

Reaction equation

HRID 890833 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.C(=O)([O-])[O-].[K+].[K+].C1O[CH2:36][CH2:35]OCCOCCOCCOCCOC1>ClC1C=CC=CC=1Cl.[Cu]>[N:12]1[CH:36]=[CH:35][CH:9]=[CH:10][C:11]=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

6

Reactant 3

HCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 2855718-Crown-6

Product 1

HCID 101017639-(pyridin-2-yl)-9H-carbazoleYield 93%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

In 40 ml of o-dichlorobenzene as solvent, 3.94 g of carbazole, 7.26 g of 2-iondopyridine, 13.10 g of potassium carbonate, 3 g of copper powder, and 0.62 g of 18-crown-6-ether were mixed and refluxed under a nitrogen atmosphere for 10 hours. Thereafter, copper and inorganic salts were removed, and the mixture was purified by column chromatography. Consequently, ligand Hpcz (9-(2-pyridyl)carbazole) was obtained (opal powder, the yield: 93%). The following is the synthesis scheme (b-1).

Workup

  1. temperaturerefluxed under a nitrogen atmosphere for 10 hours
  2. customThereafter, copper and inorganic salts were removed
  3. customthe mixture was purified by column chromatography

Sources & evidence

ORD record
ord-47da6da5fdce4132afdbfda113ab0dde
Source dataset
uspto-grants-2006_02
Patent number
US06998492B2

Reaction notes

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