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 478264Notes

Reaction equation

HRID 478264 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-e78967712d224abda17086bd59a3bf01
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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