HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 5-(4-Chlorophenyl)-2-trimethylsilanylethynylpyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 5-(4-Chlorophenyl)-2-iodopyridine | HCID 85969849 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-(4-Chlorophenyl)-2-trimethylsilanylethynylpyridine | HCID 67363611 | — |
Reaction Steps
34.9 mL (250 mmol) triethylamine and 20.8 mL (150.0 mmol) ethynyl-trimethyl-silane are added successively to a solution of 34 g (110 mmol) 5-(4-chloro-phenyl)-2-iodo-pyridine in 300 mL acetonitrile and 150 mL THF under an argon atmosphere. Then 803 mg (1.10 mmol) Pd(dppf)Cl2 and 209 mg (1.10 mmol) CuI are added. The reaction solution is stirred overnight at RT. The solvent is eliminated i.vac. and further purification is carried out by column chromatography on silica gel (PE/EtOAc 8:2).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07452911B2 |
| Source dataset | uspto-grants-2008_11 |
| ORD ID | ord-ab9d24d6c76d49ebb34224190e1283fe |
| Source note | uspto-grants-2008_11 |