HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilylacetylene → HCID 59457700, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 7-(2-Fluoro-4-nitrophenoxy)-2-iodothieno[3,2-b]pyridine | HCID 59457661 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59457700 | HCID 59457700 | 53% |
Reaction Steps
To a solution of the iodide 408 (4.5 g, 10.8 mmol) in dry THF (120 ml) at was added CuI (205 mg, 0.1 eq, 1.08 mmol), TEA (2.73 g, 2.5 eq, 27 mmol), ethynyltrimethylsilane (2.12 g, 2 eq, 21.6 mmol) and Pd(PPh3)2Cl2 (212 mg, 0.028 eq, 0.30 mmol) and the reaction mixture was heated to reflux for 2 hours. It was then cooled to RT and partitioned between EtOAc and water. The organic phase was collected, dried over anhydrous sodium sulfate, filtered and adsorbed onto silica gel. Purification by column chromatography (30% EtOAc/hexane) afforded 409 (2.2 g, 53% yield). LCMS: 387.1 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07790729B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-235cdba7cc8947108ab901a4e0f4a737 |
| Source note | uspto-grants-2010_09 |