HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → Ethyl 4-((S)-(2,4-difluorophenyl)((S)-1,1-dimethylethylsulfinamido)methyl)phenyl(methyl)phosphinate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (S)-N-((S)-(4-bromophenyl)(2,4-difluorophenyl)methyl)-2-methylpropane-2-sulfinamide | HCID 89462687 | — |
| Reactant | HCID 178476778 | HCID 178476778 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Ethyl 4-((S)-(2,4-difluorophenyl)((S)-1,1-dimethylethylsulfinamido)methyl)phenyl(methyl)phosphinate | HCID 89472304 | 44% |
Reaction Steps
To (S)—N—((S)-(4-bromophenyl)(2,4-difluorophenyl)methyl)-2-methylpropane-2-sulfinamide, 21-b, (2 g, 5 mmol), ethyl methylphosphite (1.08 g, 10 mmol) and Et3N (1.25 g, 12.5 mmol) in THF (20 ml) was added PdCl2(dppf) (360 mg). The mixture was allowed to stir overnight at reflux. The mixture was filtered and the filtrate was concentrated under vacuum. The residue was taken into ethyl acetate and washed with brine. The organic layer was concentrated under vacuum and the residue was purified over silica gel (dichloromethane:methanol=50/1) to provide the product, 21-c, (950 mg, 44%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09079930B2 |
| Source dataset | uspto-grants-2015_07 |
| ORD ID | ord-87f739a1c35e47b4b1fb5c1ff75b438c |
| Source note | uspto-grants-2015_07 |