Carbazole → HCID 57958074, compound

HRID 1022359Notes

Reaction equation

HRID 1022359 reaction equation
[C@@H]1(N)CCCC[C@H]1N.Br[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[N:11]=1.[CH:17]1[C:29]2[NH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]=2[CH:20]=[CH:19][CH:18]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu]I.O1CCOCC1>[Br:16][C:12]1[N:11]=[C:10]([N:28]2[C:29]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[C:22]3[C:27]2=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 122742,6-DibromopyridineHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 57958074HCID 57958074, compoundYield 70.5%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

Under a nitrogen atmosphere, 1.0 g (0.0088 mol) of trans-1,2-cyclohexanediamine was added to a mixture of 14.2 g (0.060 mol) of 2,6-dibromopyridine, 5.0 g (0.036 mol) of carbazole, 0.17 g (0.0019 mol) of copper(I) iodide, 31.8 g (0.15 mol) of tripotassium phosphate, and 300 ml of dehydrated 1,4-dioxane at room temperature with stirring and the mixture was heated with stirring under reflux at 100° C. for 6 hours. The reaction solution was cooled to room temperature, the inorganic salts were filtered off, and the solvent was distilled off under reduced pressure. The residue was dissolved in 200 ml of dichloromethane and washed twice with 100 ml of distilled water. The organic layer was dried over anhydrous magnesium sulfate, the magnesium sulfate was filtered off, and the solvent was distilled off under reduced pressure. The residue thus obtained was purified by reslurrying in methanol with application of heat to yield 8.2 g of 9-(6-bromo-2-pyridyl)carbazole.

Workup

  1. temperaturethe mixture was heated
  2. stirringwith stirring
  3. temperatureThe reaction solution was cooled to room temperature
  4. filtrationthe inorganic salts were filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. dissolutionThe residue was dissolved in 200 ml of dichloromethane
  7. washwashed twice with 100 ml of distilled water
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. filtrationthe magnesium sulfate was filtered off
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe residue thus obtained
  12. customwas purified
  13. temperatureof heat

Sources & evidence

ORD record
ord-3185a869bc994d0892ac5019f757a7b8
Source dataset
uspto-grants-2014_05
Patent number
US08722208B2

Reaction notes

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