Methyl iodide → HCID 90409944, compound

HRID 594046Notes

Reaction equation

HRID 594046 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([OH:9])[CH:3]=1.[C:10](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]([CH3:10])[C:4](=[O:9])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178515445HCID 178515445, compound

Product 1

HCID 90409944HCID 90409944, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-6-chloropyridin-2-ol (1.0 equiv.) in DMF (0.16 M) was added potassium carbonate (2.0 equiv.) and iodomethane (1.2 equiv.) at room temperature. The solution was stirred for 2 hours, then partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate two more times, the organic phase was washed with brine, dried with sodium sulfate, filtered and concentrated. The crude material was purified via silica gel column chromatography eluting with ethyl acetate and heptanes (0-50% ethyl acetate). The pure fractions were concentrated to yield 4-bromo-6-chloro-1-methylpyridin-2(1H)-one in 38% yield. LCMS (m/z) (M+H)=221.9/223.9, Rt=0.64 min.

Workup

  1. custompartitioned between water and ethyl acetate
  2. extractionThe aqueous phase was extracted with ethyl acetate two more times
  3. washthe organic phase was washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified via silica gel column chromatography
  8. washeluting with ethyl acetate and heptanes (0-50% ethyl acetate)
  9. concentrationThe pure fractions were concentrated

Sources & evidence

ORD record
ord-25bee3840dcf4725a1e847164ae23259
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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