HuagongsheHuagongshe Chemistry Print Report · For research reference only
Vinyl chloroformate → vinyl 10-(3-bromo-4-fluorophenyl)-9-oxo-3,4,6,8,9,10-hexahydro-2H-thiopyrano[3,2-b][1,7]naphthyridine-7(5H)-carboxylate 1,1-dioxide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Vinyl chloroformate | HCID 78808 | — |
| Reactant | 7-benzyl-10-(3-bromo-4-fluorophenyl)-3,4,6,7,8,10-hexahydro-2H-thiopyrano[3,2-b][1,7]naphthyridin-9(5H)-one 1,1-dioxide | HCID 11409753 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | vinyl 10-(3-bromo-4-fluorophenyl)-9-oxo-3,4,6,8,9,10-hexahydro-2H-thiopyrano[3,2-b][1,7]naphthyridine-7(5H)-carboxylate 1,1-dioxide | HCID 11179488 | 54.6% |
Reaction Steps
A solution of the product from Example 9A 0.48 g, 0.92 mmol) in THF (5 mL) was treated with vinyl chloroformate (0.10 mL, 0.94 mmol) and stirred at ambient temperature overnight. The solvent was evaporated and the residue was purified by flash chromatography over silica gel (ethyl acetate and then 10% ethanol/methylene chloride) to provide the title compound (0.25 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06191140B1 |
| Source dataset | uspto-grants-2001_02 |
| ORD ID | ord-6c3a3a8bcfe94559b72a6d4e24678ad2 |
| Source note | uspto-grants-2001_02 |