HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylamine → Methyl 2-(2-fluorophenylamino)-3,4-difluoro-5-((trimethylsilyl)ethynyl)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Methyl 5-bromo-2-(2-fluorophenylamino)-3,4-difluorobenzoate | HCID 59519391 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 2-(2-fluorophenylamino)-3,4-difluoro-5-((trimethylsilyl)ethynyl)benzoate | HCID 59519400 | 85% |
Reaction Steps
A mixture of methyl 5-bromo-3,4-difluoro-2-(2-fluorophenylamino)benzoate (2.70 g, 7.50 mmol), trimethylsilylacetylene (1.23 ml, 8.63 mmol), CuI (143 mg, 0.75 mmol), dichlorobis(triphenylphosphine)palladium (526 mg, 0.75 mmol) and i-Pr2NH (2.12 ml, 15.0 mmol) in THF (40 ml) was stirred at room temperature for 16 h. The reaction was concentrated and diluted with EtOAc (100 ml). The organic solution was washed with saturated aqueous NH4Cl (50 ml), dried over Na2SO4 and concentrated. Silica gel chromatography (EtOAc:Hexanes=5:95) yielded 2.40 g (85%) of methyl 3,4-difluoro-2-(2-fluorophenylamino)-5-((trimethylsilyl)ethynyl)benzoate as a tan solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08063049B2 |
| Source dataset | uspto-grants-2011_11 |
| ORD ID | ord-41f4b068b8f54983a4b3cb4129a1d962 |
| Source note | uspto-grants-2011_11 |