HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Diaminocyclohexane → 9-(9-Tosyl-carbazol-3-yl)-pyrido[2,3-b]indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Diaminocyclohexane | HCID 4610 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 9H-Pyrido(2,3-b)indole | HCID 67486 | — |
| Reactant | N-tosyl-3-iodocarbazole | HCID 66974690 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | M-Xylene | HCID 7929 | — |
| Product | 9-(9-Tosyl-carbazol-3-yl)-pyrido[2,3-b]indole | HCID 70815224 | — |
Reaction Steps
The synthesis of N-tosyl-3-iodocarbazole is described in WO2009/086028. Into a 250 mL flask was added 9H-pyrido[2,3-b]indole (5 g, 29.7 mmol), N-tosyl-3-iodocarbazole (14.63 g, 32.7 mmol), copper(I) iodide (0.283 g, 1.486 mmol) and potassium phosphate (13.25 g, 62.4 mmol). It was degassed before the addition of anhydrous m-xylene (150 mL) and cyclohexane-1,2-diamine (0.339 g, 2.97 mmol). The resultant green suspension was refluxed for three days. Column chromatography on silica gel (eluent hexane/DCM 1:4, v/v) provided the product 9-(9-tosyl-carbazol-3-yl)-pyrido[2,3-b]indole (9.9 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08580399B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-834e106a02774db4b6daf837a13c0321 |
| Source note | uspto-grants-2013_11 |