Methyl iodide → 5-Bromo-1-methylpyridin-2(1H)-one

HRID 919292Notes

Reaction equation

HRID 919292 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8]C)=[N:6][CH:7]=1.IC.[CH3:12]C(O[K])=O>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH3:12])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 27348955-Bromo-2-methoxypyridineHCID 178476685HCID 178476685, compound

Product 1

HCID 130240275-Bromo-1-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-bromo-2-methoxypyridine (1) (500 mg, 2.66 mmol), iodomethane (755 mg, 5.32 mmol) and CH3COOK (782 mg, 7.98 mmol) in acetonitrile (5 mL) was heated at reflux for 18 h. After cooled to rt, the mixture was filtered. The filtrate was concentrated and purified by reverse phase silica gel (MeOH in 0.05% NH3.H2O/H2O 10-95% v/v as mobile phase) to afford 2 as a white solid. ESI-MS: 189.0 (M+1)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. filtrationthe mixture was filtered
  4. concentrationThe filtrate was concentrated
  5. custompurified by reverse phase silica gel (MeOH in 0.05% NH3.H2O/H2O 10-95% v/v as mobile phase)

Sources & evidence

ORD record
ord-c67a19e1d6f4461cacf9a8d8b053132a
Source dataset
uspto-grants-2016_03
Patent number
US09273033B2

Reaction notes

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