Methyl iodide → N-(5-Bromo-4-methyl-2-pyridinyl)-N-methylmethanesulfonamide

HRID 1694762Notes

Reaction equation

HRID 1694762 reaction equation
[Br:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[N:6][CH:7]=1.[C:14](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[Br:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([N:8]([CH3:14])[S:9]([CH3:12])(=[O:10])=[O:11])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67280818N-(5-bromo-4-methylpyridin-2-yl)methanesulfonamide

Product 1

HCID 67280607N-(5-Bromo-4-methyl-2-pyridinyl)-N-methylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from step (i) (2.23 g), potassium carbonate (2.33 g) and methyl iodide (0.7 ml) were stirred in DMF (20 ml) for 20 h. The reaction was quenched with water, extracted with EtOAc, dried (MgSO4) and evaporated. The residue was purified by chromatography on silica eluting with 30% EtOAc/isohexane. Yield 1.5 g. Carried forward to step (ii) without characterisation.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by chromatography on silica eluting with 30% EtOAc/isohexane

Sources & evidence

ORD record
ord-162851ddd35c48c4be538806b1fc5bdf
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

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