Toluene → 5-Fluoro-N-(4-hydroxymethyl-2-methanesulfonylphenyl)-3-methylbenzo[b]thiophene-2-sulfonamide

HRID 1790237Notes

Reaction equation

HRID 1790237 reaction equation
C1(C)C=CC=CC=1.[F:8][C:9]1[CH:36]=[CH:35][C:12]2[S:13][C:14]([S:17]([NH:20][C:21]3[CH:30]=[CH:29][C:24]([C:25](OC)=[O:26])=[CH:23][C:22]=3[S:31]([CH3:34])(=[O:33])=[O:32])(=[O:19])=[O:18])=[C:15]([CH3:16])[C:11]=2[CH:10]=1.[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C(OCC)(=O)C.O>[F:8][C:9]1[CH:36]=[CH:35][C:12]2[S:13][C:14]([S:17]([NH:20][C:21]3[CH:30]=[CH:29][C:24]([CH2:25][OH:26])=[CH:23][C:22]=3[S:31]([CH3:34])(=[O:33])=[O:32])(=[O:19])=[O:18])=[C:15]([CH3:16])[C:11]=2[CH:10]=1

Participants

7

Reactant 4

HCID 1140Toluene2×HCID 9825353Methyl 4-(5-fluoro-3-methylbenzo[b]thiophene-2-sulfonylamino)-3-methanesulfonylbenzoateHCID 9855836Potassium sodium tartarateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 220414435-Fluoro-N-(4-hydroxymethyl-2-methanesulfonylphenyl)-3-methylbenzo[b]thiophene-2-sulfonamideYield 70.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-30 °C

Procedure

Into 120 mL of toluene was dissolved 2.08 g of Compound 17. After cooling to −30° C., 22.5 mL of 1.01 mol/L toluene solution of diisobutylaluminum hydride was added thereto. After 5 hours of stirring at the same temperature, water was added to the reaction solution to terminate the reaction and then the mixture was diluted with ethyl acetate, followed by addition of saturated aqueous potassium sodium tartrate solution and 30 minutes of stirring at room temperature. The mixture was extracted with ethyl acetate and the organic layer was washed with saturated brine 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 (ethyl acetate/hexane=1/1) to obtain 1.38 g of the title compound as colorless powder.

Workup

  1. additionwas added to the reaction solution
  2. customto terminate
  3. customthe reaction
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed by evaporation under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-ff5388fdf5e343ff9a10e18ce76848f7
Source dataset
uspto-grants-2006_07
Patent number
US07071220B2

Reaction notes

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