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

HRID 575605Notes

Reaction equation

HRID 575605 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-8eb05e3adb2340fb8739b29553559388
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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