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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 635974Generated: October 30, 2026

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

https://huagongshe.com/reaction/635974

Reaction equation

Participants

RoleNameHCIDCharge
ReactantVinyl chloroformateHCID 78808—
Reactant7-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-dioxideHCID 11409753—
SolventTetrahydrofuranHCID 8028—
Productvinyl 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-dioxideHCID 1117948854.6%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06191140B1
Source datasetuspto-grants-2001_02
ORD IDord-6c3a3a8bcfe94559b72a6d4e24678ad2
Source noteuspto-grants-2001_02