1,4-Dioxane → HCID 70941642, compound

HRID 2402338Notes

Reaction equation

HRID 2402338 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1)=[O:4].P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:23]1[S:27][C:26]([S:28]([NH2:31])(=[O:30])=[O:29])=[CH:25][CH:24]=1.O1CCOCC1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:23]2[S:27][C:26]([S:28](=[O:30])(=[O:29])[NH2:31])=[CH:25][CH:24]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 12413045-Bromo-2-thiophenesulfonamideHCID 27347143-(Methoxycarbonyl)benzeneboronic acid

Product 1

HCID 70941642HCID 70941642, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

1,1′-Bis(diphenylphosphino)ferrocene-palladium(II) dichloride-dichloromethane complex (272 mg, 0.33 mmol), 3-methoxycarbonylphenylboronic acid (898 mg, 4.99 mmol), and tripotassium phosphate (1.41 g, 6.64 mmol) were added to a solution of commercially available 5-bromothiophene-2-sulfonamide (805 mg, 3.33 mmol) in mixture of 1,4-dioxane (10 mL) and DMF (1 mL), followed by stirring at 85° C. overnight in an argon atmosphere. The reaction solution was concentrated. A saturated aqueous solution of sodium chloride was added to the residue, followed by extraction with methylene chloride and drying over anhydrous sodium sulfate. The solvent was distilled off, and methanol was added to the residue. The precipitated solid was filtered off. The residue obtained by distilling the solvent off was subjected to purification by silica gel column chromatography to obtain 3-(5-sulfamoyl-2-thienyl)benzoic acid methyl ester (529 mg, 1.78 mmol) (yield: 53%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionA saturated aqueous solution of sodium chloride was added to the residue
  3. extractionfollowed by extraction with methylene chloride
  4. dry with materialdrying over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. additionmethanol was added to the residue
  7. filtrationThe precipitated solid was filtered off
  8. customThe residue obtained
  9. distillationby distilling the solvent
  10. customoff was subjected to purification by silica gel column chromatography

Sources & evidence

ORD record
ord-e549daeeecfb48868f5722261aaab83e
Source dataset
uspto-grants-2014_08
Patent number
US08796320B2

Reaction notes

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