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

HRID 635974Notes

Reaction equation

HRID 635974 reaction equation
C([N:8]1[CH2:17][C:16]2[NH:15][C:14]3[CH2:18][CH2:19][CH2:20][S:21](=[O:23])(=[O:22])[C:13]=3[CH:12]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[C:26]([Br:31])[CH:25]=3)[C:11]=2[C:10](=[O:32])[CH2:9]1)C1C=CC=CC=1.Cl[C:34]([O:36][CH:37]=[CH2:38])=[O:35]>C1COCC1>[Br:31][C:26]1[CH:25]=[C:24]([CH:12]2[C:11]3[C:10](=[O:32])[CH2:9][N:8]([C:34]([O:36][CH:37]=[CH2:38])=[O:35])[CH2:17][C:16]=3[NH:15][C:14]3[CH2:18][CH2:19][CH2:20][S:21](=[O:23])(=[O:22])[C:13]2=3)[CH:29]=[CH:28][C:27]=1[F:30]

Participants

4

Reactant 2

HCID 78808Vinyl chloroformateHCID 114097537-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

Product 1

HCID 11179488vinyl 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-dioxideYield 54.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography over silica gel (ethyl acetate

Sources & evidence

ORD record
ord-6c3a3a8bcfe94559b72a6d4e24678ad2
Source dataset
uspto-grants-2001_02
Patent number
US06191140B1

Reaction notes

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