Potassium Carbonate → 3-Bromo-4-[(2,4-difluorophenyl)methoxy]-1-[(3-fluorophenyl)methyl]-2(1H)-pyridinone

HRID 1866921Notes

Reaction equation

HRID 1866921 reaction equation
[Br:1][C:2]1[C:3](=[O:17])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[OH:8].C([O-])([O-])=O.[K+].[K+].[F:24][C:25]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:26]=1[CH2:27]Br>CC(C)=O>[Br:1][C:2]1[C:3](=[O:17])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:27][C:26]1[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:25]=1[F:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 54724177HCID 54724177, compound

Product 1

HCID 102165503-Bromo-4-[(2,4-difluorophenyl)methoxy]-1-[(3-fluorophenyl)methyl]-2(1H)-pyridinone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-bromo-1-(3-fluorobenzyl)-4-hydroxy-1H-pyridin-2-one (0.20 g, 0.67) and K2CO3 (0.27 g, 1.34 mmol) in acetone (10 mL) was added 2,4-difluorobenzyl bromide (0.16 g, 0.8 mmol), and the reaction mixture was heated at reflux for 1 h. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and the residue was dissolved in EtOAc. The organic solution was washed with water and then brine, dried (Na2SO4), filtered and concentrated under reduced pressure. 1H NMR (300 MHz, CDCl3) δ 7.65-7.55 (m, 1H), 7.40-7.25 (m, 2H), 7.15-6.80 (m, 5H), 6.14 (d, J=8 Hz, 1H), 5.22 (s, 2H), 5.16 (s, 2H). ESHRMS m/z 424.0159 (M+H C19H14BrF3NO2 requires 424.0155).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. concentrationconcentrated under reduced pressure
  4. dissolutionthe residue was dissolved in EtOAc
  5. washThe organic solution was washed with water
  6. dry with materialbrine, dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f04d79d86b5d48a681153b214a703a34
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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