Sodium Iodide → HCID 22041472, compound

HRID 1790233Notes

Reaction equation

HRID 1790233 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([C:18]3[S:22][C:21]4[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:20]=4[C:19]=3[CH3:28])(=[O:17])=[O:16])=[C:10]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:9]=2)[S:6][CH:7]=1.[I-].[Na+]>CC(C)=O>[F:27][C:25]1[CH:24]=[CH:23][C:21]2[S:22][C:18]([S:15]([NH:14][C:11]3[CH:12]=[CH:13][C:8]([C:5]4[S:6][CH:7]=[C:3]([CH3:2])[N:4]=4)=[CH:9][C:10]=3[S:29]([CH3:32])(=[O:31])=[O:30])(=[O:16])=[O:17])=[C:19]([CH3:28])[C:20]=2[CH:26]=1

Participants

4

Reactant 2

HCID 5238Sodium Iodide2×HCID 22041461HCID 22041461, compound

Product 1

HCID 22041472HCID 22041472, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into 10 mL of acetone was dissolved 64 mg of Compound 64, and 180 mg of sodium iodide was added, followed by 24 hours of heating under refluxing. Further, 180 mg of sodium iodide was added and the mixture was heated under refluxing for 19 hours. The solvent was removed by evaporation under reduced pressure and the residue was dissolved into ethyl acetate. The solution was washed with water, 5% aqueous sodium thiosulfate solution, water and saturated brine, successively, and then dried over anhydrous sodium sulfate. After the solvent was removed by evaporation under reduced pressure, the resulting 5-fluoro-N-[4-(4-iodomethylthiazol-2-yl)-2-methanesulfonylphenyl]-3-methylbenzo[b]thiophene-2-sulfonamide was dissolved into a mixed solution of 5 mL of toluene and 0.5 mL of DMSO, and 45 μL of tributyltin hydride and 13 μL of 1.06 mol/L hexane solution of triethylboron were added, followed by 6 hours of stirring at room temperature. Further, 24 μl of tributyltin hydride was added and the mixture was stirred at room temperature for 3 hours. Then, the reaction was terminated by adding saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, successively, and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane to hexane/ethyl acetate=3/1) to obtain 29 mg of the title compound as colorless powder.

Workup

  1. additionwas added
  2. temperatureof heating
  3. temperatureunder refluxing
  4. temperaturethe mixture was heated
  5. temperatureunder refluxing for 19 hours
  6. customThe solvent was removed by evaporation under reduced pressure
  7. dissolutionthe residue was dissolved into ethyl acetate
  8. washThe solution was washed with water, 5% aqueous sodium thiosulfate solution, water and saturated brine
  9. dry with materialsuccessively, and then dried over anhydrous sodium sulfate
  10. customAfter the solvent was removed by evaporation under reduced pressure
  11. dissolutionthe resulting 5-fluoro-N-[4-(4-iodomethylthiazol-2-yl)-2-methanesulfonylphenyl]-3-methylbenzo[b]thiophene-2-sulfonamide was dissolved into a mixed solution of 5 mL of toluene and 0.5 mL of DMSO, and 45 μL of tributyltin hydride and 13 μL of 1.06 mol/L hexane solution of triethylboron
  12. additionwere added
  13. waitfollowed by 6 hours
  14. additionFurther, 24 μl of tributyltin hydride was added
  15. stirringthe mixture was stirred at room temperature for 3 hours
  16. customThen, the reaction was terminated
  17. additionby adding saturated aqueous ammonium chloride solution
  18. extractionfollowed by extraction with ethyl acetate
  19. washThe organic layer was washed with water and saturated brine
  20. dry with materialsuccessively, and then dried over anhydrous sodium sulfate
  21. customThe solvent was removed by evaporation under reduced pressure
  22. customthe resulting residue was purified by silica gel column chromatography (hexane to hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-41efe53e0c8b4b2eb8ad50e1253946aa
Source dataset
uspto-grants-2006_07
Patent number
US07071220B2

Reaction notes

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