Carbazole → HCID 68603418, compound

HRID 1893103Notes

Reaction equation

HRID 1893103 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[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](Br)=[CH:17][CH:16]=1.N[CH:27](N)[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[C:15]1([C:27]2[CH:32]=[CH:31][C:30]([C:8]3[CH:7]=[C:6]4[C:11](=[CH:10][CH:9]=3)[NH:12][C:13]3[CH:1]=[CH:2][C:3]([C:1]5[CH:13]=[CH:5][CH:4]=[CH:3][CH:2]=5)=[CH:4][C:5]4=3)=[CH:29][CH:28]=2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

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

Product 1

HCID 68603418HCID 68603418, compoundYield 6%

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 6, a solution of 10 g (31.3 mmol) of carbazole, 13.5 g (31.3 mmol) of 1,4-dibromonaphthalene, CuI, diaminohexane and K3PO4 in dioxane was 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: 6%. MS (EI) (Calcd. for C34H22BrN: 523.09. Found: 523).

Workup

  1. customAs depicted in Reaction 6
  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-da1f874af74444b19b1abdb3246d5ef8
Source dataset
uspto-grants-2013_08
Patent number
US08512877B2

Reaction notes

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