Potassium Carbonate → HCID 66685239, compound

HRID 1778401Notes

Reaction equation

HRID 1778401 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[Br:23])(=[O:15])=[O:14])[CH:5]=[CH:4][C:3]=1[C:24]1[CH:28]=[CH:27][O:26][C:25]=1[C:29]([O:31]CC)=O.C(=O)([O-])[O-].[K+].[K+]>CO>[Br:23][C:17]1[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]=1[S:13]([NH:12][C:6]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:2]2[C:3]([C:24]3[CH:28]=[CH:27][O:26][C:25]=3[C:29](=[O:31])[NH:1]2)=[CH:4][CH:5]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 66685755HCID 66685755, compound2×

Product 1

HCID 66685239HCID 66685239, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 3-[2-amino-4-(2-bromo-4-fluorobenzenesulfonylamino)-3-methoxycarbonylphenyl]-furan-2-carboxylate (Intermediate 88, 0.960 g) and potassium carbonate (0.736 g) in methanol (50 mL) was heated at reflux overnight. The resultant mixture was concentrated in vacuo and the residue was acidified with 1M HCl and extracted with a mixture of DCM and ethyl acetate. The precipitate from the acidification did not dissolve, therefore the volatiles were removed in vacuo and the aqueous slurry was filtered. The resultant paste was triturated with hot acetonitrile and the solid was collected by filtration and dried under vacuum overnight. The resultant solid was purified by chromatography on silica, eluting with a mixture of ethyl acetate and DCM, with a gradient of 0-100%, followed by methanol and DCM, with a gradient of 0-10% and finally flushing the column with methanol and DCM (50%) to give methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-4-oxo-4,5-dihydrofuro[2,3-c]quinoline-6-carboxylate (0.685 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe resultant mixture was concentrated in vacuo
  4. extractionextracted with a mixture of DCM and ethyl acetate
  5. dissolutionThe precipitate from the acidification did not dissolve
  6. customthe volatiles were removed in vacuo
  7. filtrationthe aqueous slurry was filtered
  8. customThe resultant paste was triturated with hot acetonitrile
  9. filtrationthe solid was collected by filtration
  10. customdried under vacuum overnight
  11. customThe resultant solid was purified by chromatography on silica
  12. washeluting with a mixture of ethyl acetate and DCM, with a gradient of 0-100%
  13. customfinally flushing the column with methanol and DCM (50%)

Sources & evidence

ORD record
ord-f699b69ab57841dbbbb60682aa42bd6a
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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