Dimethylformamide → HCID 23028709, compound

HRID 2080430Notes

Reaction equation

HRID 2080430 reaction equation
[CH3:1]N(C)C=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH:16]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[H-].[Na+].CI>CCCCCC.O>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([C:16]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=2)([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[F:31])[CH3:1])(=[O:14])=[O:15])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23114561HCID 23114561, compound

Product 1

HCID 23028709HCID 23028709, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent2×

Procedure

An N,N-dimethylformamide (5 ml) solution of the 2-[[(4-chlorophenyl)sulfonyl](2,5-difluorophenyl)methyl]-5-methylpyridine (52 mg, 0.132 mmol) obtained in Example 15 was added dropwise to an N,N-dimethylformamide (5 ml) suspension of sodium hydride (60% in oil) (30 mg, 0.75 mmol) under ice cooling. After the reaction mixture was stirred for 15 minutes under ice cooling, methyl iodide (12 μl, 0.198 mmol) was added thereto. After stirring at room temperature for 1 hour, water was added to the reaction mixture under ice cooling. The resulting mixture was concentrated under reduced pressure. To the residue was added water and the resulting mixture was extracted 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 silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=8:1 eluate was concentrated under reduced pressure. The residue thus obtained was solidified with hexane and collected by filtration to give the title compound (50 mg, 0.122 mmol, 93%) as a white powder.

Workup

  1. stirringAfter stirring at room temperature for 1 hour
  2. concentrationThe resulting mixture was concentrated under reduced pressure
  3. additionTo the residue was added water
  4. extractionthe resulting mixture was extracted 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 eluate was concentrated under reduced pressure
  11. customThe residue thus obtained
  12. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c6d99ed8da2648eeb05f02e3f1a074ff
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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