HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetanilide → HCID 15151164, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetanilide | HCID 904 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Phenylacetylene | HCID 10821 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Solvent | 1,1,3,3-Tetramethylguanidine | HCID 66460 | — |
| Product | HCID 15151164 | HCID 15151164 | 82% |
Reaction Steps
Following the procedure of A. Bedeschi et al. (Tet. Lett. 1997, 38, 2307), the acetanilide derivative from above (0.900 g, 2.7 mmol) was reacted with phenylacetylene (0.385 mL, 3.5 mmol, 1.3 equivalent) in the presence of PdCl2(PPh3)2 (10 mole %) and CuI (10 mole %) in a mixture of dioxane (5 mL) and tetramethylguanidine (5 mL). The desired 2-phenylindole (0.589 g, 82% yield) was isolated as a yellow solid after flash chromatography with 15% EtOAc in hexane.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07141574B2 |
| Source dataset | uspto-grants-2006_11 |
| ORD ID | ord-0bb3e91adf5549b98cb0942706b61ce5 |
| Source note | uspto-grants-2006_11 |