HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-Methoxy-2-(3-methylbut-1-ynyl)aniline → 2-Isopropyl-6-methoxy-1H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-Methoxy-2-(3-methylbut-1-ynyl)aniline | HCID 59762435 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-Isopropyl-6-methoxy-1H-indole | HCID 59762448 | — |
Reaction Conditions
| Temperature | 160 °C |
|---|
Reaction Steps
To a solution of 5-methoxy-2-(3-methylbut-1-ynyl)aniline (Compound 135, 1.8 g, 9.5 mmol) in DMF (20 ml) was added CuI (101 mg, 0.53 mmol). The reaction was stirred at 160° C. for 1.5 h. The solvent was removed in vacuo and the residue was purified by chromatography on silica gel (0→25% EtOAc-hexanes) to yield the title compound as a brownish red solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08524917B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-d729692a87884250a6619b9f8339b84e |
| Source note | uspto-grants-2013_09 |