Methyl iodide → 6-Iodo-2-methyl[1,2,4]triazolo[4,3-alpha]pyridin-3(2H)-one

HRID 1372483Notes

Reaction equation

HRID 1372483 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](=[O:11])[NH:9][N:10]=2)[CH:7]=1.[C:12](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C)C=O.C(OCC)(=O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](=[O:11])[N:9]([CH3:12])[N:10]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 587793486-Iodo-[1,2,4]triazolo[4,3-a]pyridin-3(2h)-one2×

Product 1

HCID 587793506-Iodo-2-methyl[1,2,4]triazolo[4,3-alpha]pyridin-3(2H)-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-iodo[1,2,4]triazolo[4,3-α]pyridin-3(2H)-one (Intermediate 13, 360 mg, 1.379 mmol) in anhydrous dimethylformamide (DMF, 4 mL) was added sequentially cesium carbonate (1.35 g, 4.14 mmol) and iodomethane (0.52 mL), and the reaction mixture was stirred at room temperature overnight. The reaction mixture was then diluted with ethyl acetate, and the precipitated solids were removed by filtration. The filtrate was washed with saturated aqueous brine, dried (magnesium sulfate), and concentrated to dryness under reduced pressure. The residue was purified by preparative thin layer chromatography (silica gel, 3% methanol/dichloromethane) to afford the title compound. LC/MS 257.8 (M+1).

Workup

  1. customthe precipitated solids were removed by filtration
  2. washThe filtrate was washed with saturated aqueous brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue was purified by preparative thin layer chromatography (silica gel, 3% methanol/dichloromethane)

Sources & evidence

ORD record
ord-6f3ecbf5cd1b4f94aaa29deeda708210
Source dataset
uspto-grants-2007_01
Patent number
US07157490B2

Reaction notes

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