HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclopropylacetylene → [4-(tert-Butyldimethylsilanyloxy)cyclohexyl]-(2-cyclopropylethynylphenyl)amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclopropylacetylene | HCID 138823 | — |
| Reactant | [4-(Tert-butyldimethylsilanyloxy)cyclohexyl]-(2-iodophenyl)amine | HCID 57675754 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | [4-(tert-Butyldimethylsilanyloxy)cyclohexyl]-(2-cyclopropylethynylphenyl)amine | HCID 57675733 | — |
Reaction Steps
To a solution of [4-(tert-butyldimethylsilanyloxy)cyclohexyl]-(2-iodophenyl)amine (4.47 g, 10.4 mmol) in triethylamine (70 mL) was added copper(I) iodide (198 mg, 1.04 mmol), followed by bis(triphenylphosphine)palladium(II) chloride (730 mg, 1.04 mmol) and cyclopropylacetylene (1.73 mL, 20.8 mmol). The reaction was stirred under nitrogen at room temperature overnight. After the reaction mixture was concentrated, the residue was dissolved in ether and filtered through Celite. Concentration gave the crude product, which was used without further purification in quantitative yield. LC-MS (C23H35NOSi calc'd 369) m/z 370 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08129424B2 |
| Source dataset | uspto-grants-2012_03 |
| ORD ID | ord-1ca27ab960744b79827b49d4e29395ee |
| Source note | uspto-grants-2012_03 |