Water → 5-Bromo-3-fluoro-1-methylpyridin-2(1H)-one

HRID 518335Notes

Reaction equation

HRID 518335 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:9])[C:5]([OH:8])=[N:6][CH:7]=1.IC.[C:12]([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([F:9])[C:5](=[O:8])[N:6]([CH3:12])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1785175945-Bromo-3-fluoro-1,2-dihydropyridin-2-one

Product 1

HCID 707010305-Bromo-3-fluoro-1-methylpyridin-2(1H)-oneYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-bromo-3-fluoropyridin-2-ol (1 g, 5.2 mmol), iodomethane (356 mg, 5.7 mmol) and K2CO3 (1.4 g, 10.4 mmol) in DMF (10 mL) was stirred at rt for 12 h. The mixture was treated with water (70 ml) and extracted with EtOAc (3×50 ml). The combined organic extracts were washed with saturated bicarbonate solution (aq), dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound (1 g, 93%) as a white solid which was carried forward without purification. LCMS (M+H)+=207.

Workup

  1. extractionextracted with EtOAc (3×50 ml)
  2. washThe combined organic extracts were washed with saturated bicarbonate solution (aq)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e3332fcd5e04444ca143d62b00985c16
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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