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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 478264Generated: October 29, 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/478264

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 numberUS06642222B2
Source datasetuspto-grants-2003_11
ORD IDord-e78967712d224abda17086bd59a3bf01
Source noteuspto-grants-2003_11