Water → HCID 23028709, compound

HRID 748864Notes

Reaction equation

HRID 748864 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])[C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:29]I.O>CN(C)C=O.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])[CH3:29])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23114561HCID 23114561, compound

Product 1

HCID 23028709HCID 23028709, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent2×

Procedure

Under ice cooling, a solution of the 2-[[(4-chlorophenyl)sulfonyl](2,5-difluorophenyl)methyl]-5-methylpyridine (52 mg, 0.132 mmol), which had been obtained in Example 137, in N,N-dimethylformamide (5 ml) was added dropwise to a suspension of sodium hydride (a 60% oil dispersion, 30 mg, 0.75 mmol) in N,N-dimethylformamide (5 ml). The reaction mixture was stirred for 15 minutes under ice cooling, and then, methyl iodide (12 μl, 0.198 mmol) was added. After stirring at room temperature for 1 hour, water was added to the reaction mixture under ice cooling, followed by concentration under reduced pressure. Water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to chromatography on a silica gel column. A fraction obtained from the eluate with hexane:ethyl acetate (=8:1) was concentrated under reduced pressure. The residue thus obtained was solidified with hexane and collected by filtration, whereby the title compound (50 mg, 0.122 mmol, 93%) was obtained as a white powder.

Workup

  1. stirringAfter stirring at room temperature for 1 hour
  2. concentrationfollowed by concentration under reduced pressure
  3. additionWater was added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customThe residue thus obtained
  10. concentrationethyl acetate (=8:1) was concentrated under reduced pressure
  11. customThe residue thus obtained

Sources & evidence

ORD record
ord-02d40998dce5401fb93763cdc2f783eb
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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