Methyl iodide → Methyl 2-chloro-6-[methyl(methylsulfonyl)amino]isonicotinate

HRID 732441Notes

Reaction equation

HRID 732441 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:18])[C:6]1[CH:11]=[C:10]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[N:9]=[C:8]([Cl:17])[CH:7]=1.I[CH3:20]>CN(C=O)C>[CH3:3][O:4][C:5](=[O:18])[C:6]1[CH:11]=[C:10]([N:12]([S:13]([CH3:16])(=[O:14])=[O:15])[CH3:20])[N:9]=[C:8]([Cl:17])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86615008Methyl 2-chloro-6-methanesulphonylamino-isonicotinate

Product 1

HCID 86612064Methyl 2-chloro-6-[methyl(methylsulfonyl)amino]isonicotinateYield 72.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Add sodium hydride (257 mg, 6.43 mmol, 60% dispersion in mineral oil) at 0° C. to a solution of 2-chloro-6-methanesulfonylamino-isonicotinic acid methyl ester (1.31 g, 4.95 mmol) in DMF (10 mL). After stirring at 0° C. for 15 min, add iodomethane (0.4 mL, 6.43 mmol). Stir the reaction at 0° C. for 1 h and at room temperature for 2 h. Quench the reaction with ice and extract the reaction mixture with ethyl acetate. Wash the organic layer with saturated aqueous sodium chloride, dry (sodium sulfate), concentrate and purify (silica gel chromatography, eluting with 30:70 ethyl acetate:hexanes) to give the title compound (1.0 g, 72%).

Workup

  1. stirringStir
  2. customthe reaction at 0° C. for 1 h
  3. waitat room temperature for 2 h
  4. customQuench
  5. customthe reaction with ice
  6. extractionextract the reaction mixture with ethyl acetate
  7. washWash the organic layer with saturated aqueous sodium chloride
  8. dry with materialdry (sodium sulfate)
  9. concentrationconcentrate
  10. custompurify
  11. wash(silica gel chromatography, eluting with 30:70 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-c686f007f0324dbcb02d2f1c4c0603ba
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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