Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Carbazole | HCID 6854 | — |
| Reactant | 2,6-Dibromopyridine | HCID 12274 | — |
| Reactant | 1,2-Diaminocyclohexane, trans- | HCID 43806 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 57958074 | HCID 57958074 | 70.5% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08722208B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-3185a869bc994d0892ac5019f757a7b8 |
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| Source note | uspto-grants-2014_05 |
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