HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3-(2-Pyrrolidinylethyl)-1-(p-toluenesulfonyl)-5-(triethylsilylethynyl)-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (Triethylsilyl)acetylene | HCID 637947 | — |
| Reactant | 5-Bromo-3-(2-pyrrolidinylethyl)-1-(p-toluene-sulfonyl)-indole | HCID 15838486 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 3-(2-Pyrrolidinylethyl)-1-(p-toluenesulfonyl)-5-(triethylsilylethynyl)-indole | HCID 15838487 | 39% |
Reaction Steps
To a solution of 5-bromo-3-(2-pyrrolidinylethyl)-1-(p-toluenesulfonyl)-indole (Example 5, 415 mg, 1 mmol) in toluene (20 mL), were added triethylsilylacetylene (0.72 mL, 4 mmol, dichlorbis(triphenylphosphine) palladium (II) (210 mg, 0.3 mmol), copper (I) iodide (57 mg, 0.3 mmol) and triethylamine (1 mL). The resulting mixture was stirred under argon at reflux overnight and then evaporated to dryness. Chromatography on silica gel (ethyl acetate followed by methanol) gave the title compound as a yellow oil (197 mg, 39%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05856510 |
| Source dataset | uspto-grants-1999_01 |
| ORD ID | ord-b7616756be1a48adaf86d419002a3d66 |
| Source note | uspto-grants-1999_01 |