Methyl iodide → 5-iodo-1,3-dimethylpyridin-2(1H)-one

HRID 873823Notes

Reaction equation

HRID 873823 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([OH:8])=[N:6][CH:7]=1.[C:10]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5](=[O:8])[N:6]([CH3:10])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178427896HCID 178427896, compound

Product 1

HCID 904273665-iodo-1,3-dimethylpyridin-2(1H)-oneYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 5-iodo-3-methylpyridin-2-ol (Step 23.1) (1.67 g, 7.11 mmol) and K2CO3 (1.964 g, 14.21 mmol) in DMF (20 mL) was added MeI (0.666 mL, 10.66 mmol) at rt under Ar. The reaction mixture was stirred 1 hr at rt, concentrated, diluted with water, and extracted with EtOAc. The organic layers were combined and washed once with water, dried over Na2SO4 and evaporated. The crude material was purified by silica gel column chromatography (hexane/EtOAc 50-65) to afford the title product (1.40 g, 5.62 mmol, 79% yield) as a brown solid. tR: 3.31 min (HPLC 1); tR: 0.71 min (LC-MS 2); ESI-MS: 250 [M+H]+ (LC-MS 2); Rf=0.31 (hexane/EtOAc 1:1).

Workup

  1. concentrationconcentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. washwashed once with water
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe crude material was purified by silica gel column chromatography (hexane/EtOAc 50-65)

Sources & evidence

ORD record
ord-84b52ede6130417888d10631d63c7c98
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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