HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → N-[[(3S,3aS)-7-(2-methylsulfonylphenyl)-1-oxo-3a,4-dihydro-3H-[1,3]oxazolo[4,3-c][1,4]benzoxazin-3-yl]methyl]-5-chlorothiophene-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Benzene, 1-bromo-2-(methylsulfonyl)- | HCID 190318 | — |
| Reactant | 5-chloro-N-(((3S,3 aS)-1-oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)thiophene-2-carboxamide | HCID 131736053 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Product | N-[[(3S,3aS)-7-(2-methylsulfonylphenyl)-1-oxo-3a,4-dihydro-3H-[1,3]oxazolo[4,3-c][1,4]benzoxazin-3-yl]methyl]-5-chlorothiophene-2-carboxamide | HCID 118574663 | 35.2% |
Reaction Steps
Using compound 5-chloro-N-(((3S,3aS)-1-oxo-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,3a,4-tetrahydrobenzo[b]oxazolo[3,4-d][1,4]oxazin-3-yl)methyl)thiophene-2-carboxamide (the product of step (b) in Example 35) (50 mg, 0.102 mmol), o-methylsulfonylbromobenzene (29 mg, 0.122 mmol), tetrakis (triphenylphosphine) palladium (12 mg, 0.010 mmol), and cesium carbonate (66 mg, 0.204 mmol) as starting materials, preparation following the method as described in Example 35 (c) afforded off-white solid 19 mg, yield: 35.2%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09382265B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-63b99377bf65496fbe3f2ee9b3c54596 |
| Source note | uspto-grants-2016_07 |