HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 23502795, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | N-(3,5-Bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide | HCID 10231844 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | tert-Butyl methyl ether | HCID 15413 | — |
| Product | HCID 23502795 | HCID 23502795 | 83.2% |
Reaction Steps
To a mixture of 200 mg (0.346 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide (Example 4), 0.073 ml (0.52 mmol) triethylamine, 5 mg (0.007 mmol) bis(triphenylphosphine)palladium(II) chloride and 3 mg (0.014 mmol) copper(I) iodide in 1 ml tetrahydrofuran a solution of 0.098 ml (0.69 mmol) trimethylsilylacetylene in 0.5 ml tetrahydrofuran was added at room temperature. After stirring for 17 h the mixture was diluted with tert-butyl methyl ether. Washing with a saturated aqueous solution of ammonium chloride was followed by drying with sodium sulfate and evaporation of the solvent. Column chromatography afforded 158 mg (83%) of the title compound as a light brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06770637B2 |
| Source dataset | uspto-grants-2004_08 |
| ORD ID | ord-1bcc6da4c75a4983827222989fef630d |
| Source note | uspto-grants-2004_08 |