HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilylacetylene → Benzyl-[1-(4-trimethylsilanylethynyl-phenyl)cyclopropyl]-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | HCID 22568916 | HCID 22568916 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | Benzyl-[1-(4-trimethylsilanylethynyl-phenyl)cyclopropyl]-amine | HCID 22568959 | 74% |
Reaction Steps
Using General Procedure D; benzyl-[1-(4-bromophenyl)-cyclopropyl]-amine (Intermediate 124, 110.0 mg, 0.36 mmol) in triethylamine (8 mL) was treated with copper(I)iodide (10.0 mg, 0.05 mmol) and then sparged with argon for 5 minutes. Trimethylsilyl acetylene (0.70 g, 7.1 mmols) was then added followed by dichlorobis(triphenylphosphine)palladium(II) (38.0 mg, 0.05 mmol). The resulting reaction mixture was heated to 70° C. for 5d. The title compound 85 mg (74%) was isolated by chromatography (1-10% EtOAc-hexanes).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06387892B1 |
| Source dataset | uspto-grants-2002_05 |
| ORD ID | ord-554f475178c04240befe77328547b30c |
| Source note | uspto-grants-2002_05 |