HuagongsheHuagongshe Chemistry Print Report · For research reference only
Indole → N-(4-methylphenyl)indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Indole | HCID 798 | — |
| Reactant | 4-Bromotoluene | HCID 7805 | — |
| 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 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | N-(4-methylphenyl)indole | HCID 9794286 | 95% |
Reaction Steps
Using the general procedure outlined in Example 63, indole (0.117 g, 1.00 mmol) was coupled with 4-bromotoluene (185 μL, 1.50 mmol) using CuI (9.5 mg, 0.050 mmol, 5.0 mol %), K3PO4 (2.1 mmol), trans-1,2-cyclohexanediamine (24 μL, 0.20 mmol, 20 mol %) and dioxane (1.0 mL) to give the crude product. Column chromatography (2×15 cm, hexane:ethyl acetate 50:1) provided 0.197 g (95% yield) of the product as a white solid. This product was pure by 1H NMR when compared to the known spetra.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06759554B2 |
| Source dataset | uspto-grants-2004_07 |
| ORD ID | ord-eabd0a33d3204f20b34c46f367121a2b |
| Source note | uspto-grants-2004_07 |