Methyl iodide → 3-Bromo-1,6-dimethylpyridin-2(1H)-one

HRID 870779Notes

Reaction equation

HRID 870779 reaction equation
[Br:1][C:2]1[C:3]([OH:9])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[H-].[Na+].[Br-].[Li+].I[CH3:15]>C1COCC1.C(Cl)Cl>[Br:1][C:2]1[C:3](=[O:9])[N:4]([CH3:15])[C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 82050Lithium BromideHCID 178423588HCID 178423588, compound

Product 1

HCID 672811503-Bromo-1,6-dimethylpyridin-2(1H)-oneYield 55.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Bromo-6-methylpyridine-2-ol (2 g, 10.6 mmol) was taken up in THF and stirred. Sodium hydride (60% in oil 510 mg, 12.7 mmol) was added portion wise then stirred 30 minutes. Lithium bromide (1.85 g, 21.2 mmol) was added and stirred for 1 hour. Then iodomethane (1.32 mL, 21.2 mmol) was added and the reaction mixture was stirred overnight. The reaction mixture was diluted with DCM and washed with 1N NaOH. The DCM layer was dried over magnesium sulfate, filtered and dried in vacuo to afford 1.19 g product carried on to next step as is. LRMS (ESI) m/z 202/204 [(M+H)]+, calc'd for C7H8BrNO: 202.05.

Workup

  1. stirringstirred 30 minutes
  2. stirringstirred for 1 hour
  3. stirringthe reaction mixture was stirred overnight
  4. washwashed with 1N NaOH
  5. dry with materialThe DCM layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-165c9804823f463082a530b6e97ed2de
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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