Water → HCID 21098652, compound

HRID 1351293Notes

Reaction equation

HRID 1351293 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:21])[CH2:9][N:10]([CH3:20])[S:11]([C:14]2[S:15][C:16]([Br:19])=[CH:17][CH:18]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:24]I.O>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:21][CH3:24])[CH2:9][N:10]([CH3:20])[S:11]([C:14]2[S:15][C:16]([Br:19])=[CH:17][CH:18]=2)(=[O:12])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21098651HCID 21098651, compound

Product 1

HCID 21098652HCID 21098652, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromothiophene-2-sulfonic acid [2-(4-fluorophenyl)-2-hydroxyethyl]-methyl-amide (the compound of Preparation Example 71) (210 mg) in N,N-dimethylformamide (2 mL) was added 60% sodium hydride (32 mg). After stirring for 45 minutes, methyl iodide (100 μL) was added. Water was added, the solution was extracted with ethyl acetate. After washing the organic layer with saturated sodium chloride water, and then was dried with anhydrous sodium sulfate, the residue that was obtained upon removal of the solvent by evaporation was purified by silica gel column chromatography (hexane/ethyl acetate), and the title compound (110 mg) was obtained as a colorless oily matter.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washAfter washing the organic layer with saturated sodium chloride water
  3. dry with materialwas dried with anhydrous sodium sulfate
  4. customthe residue that was obtained upon removal of the solvent by evaporation
  5. customwas purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4f10437ee19f4460a7fe0cc869648448
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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