Carbazole → HCID 58969344, compound

HRID 1893100Notes

Reaction equation

HRID 1893100 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:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](Br)=[CH:17][CH:16]=1.NC(N)CCCCC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[Br:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 62657Potassium Phosphate, TribasicHCID 665211,4-DibromonaphthaleneHCID 134940Hexanediamine

Product 1

HCID 58969344HCID 58969344, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

As depicted in Reaction 1, 3.3 g (20 mmol) of carbazole, 8.6 g (40 mmol) of 1,4-dibromonaphthalene, CuI, diaminohexane and K3PO4 were dissolved in dioxane and refluxed for 15 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. After the solvent was removed under reduced pressure, the residue was purified by column chromatography to give the title compound. The product was collected by filtration under reduced pressure and dried. Yield: 35%. MS (EI) (Calcd. for C22H14BrN: 371.03. Found: 371).

Workup

  1. temperaturerefluxed for 15 hours
  2. customAfter completion of the reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. customAfter the solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-2c4f7599b17b4016bc8c7c7cee076086
Source dataset
uspto-grants-2013_08
Patent number
US08512877B2

Reaction notes

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