HuagongsheHuagongshe Chemistry Print Report · For research reference only
Indole → N-(4-methylphenyl)indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Indole | HCID 798 | — |
| Reactant | 4-Chlorotoluene | HCID 7810 | — |
| 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 | Ethyl acetate hexane | HCID 21226206 | — |
| Product | N-(4-methylphenyl)indole | HCID 9794286 | — |
Reaction Steps
Using the general procedure outlined in Example 63, indole (0.117 g, 1.00 mmol) was coupled with 4-chlorotoluene (1 mL, 8.45 mmol) using CuI (9.5 mg, 0.050 mmol, 5.0 mol %), K3PO4 (2.1 mmol) and trans-1,2-cyclohexanediamine (24 μL, 0.20 mmol, 20 mol %) to give the crude product. Column chromatography (2×15 cm, hexane:ethyl acetate 50:1) provided 0.066 g (32% GC yield) of the product as a white solid. This product was pure by 1H NMR when compared to the known spectra.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07115784B2 |
| Source dataset | uspto-grants-2006_10 |
| ORD ID | ord-916c81a7bfa64ba1bbd63c6028981bb7 |
| Source note | uspto-grants-2006_10 |