Potassium Carbonate → HCID 22050777, compound

HRID 1867059Notes

Reaction equation

HRID 1867059 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH3:14])=[CH:12][C:11]([OH:15])=[CH:10][C:9]2=[O:16])=[C:4]([CH3:17])[CH:3]=1.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>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH2:27][C:26]3[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:25]=3[F:24])=[CH:10][C:9]2=[O:16])=[C:4]([CH3:17])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 54724179HCID 54724179, compound

Product 1

HCID 22050777HCID 22050777, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(4-bromo-2-methylphenyl)-4-hydroxy-6-methylpyridin-2(1H)-one (7.35 g, 25.0 mmol) was dissolved in DMF (15 mL) and stirred with potassium carbonate (4.14 g, 30.0 mmol) and 2,4 difluorobenzyl bromide (3.21 ml (25.0 mmol) at room temperature for 2 hours. The reaction was worked up by pouring in to 300 ml ice water under continuous stirring. A white precipitate was obtained which was isolated by filtering and further purified by triturating with ether to give 3.06 g (29%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 7.65-7.59 (m, 2H), 7.49 (dd, J=8.45, 2.22 Hz, 1H), 7.31 (dt, J=9.79, 2.22 Hz, 1H), 7.16-7.08 (m, 2H), 6.05 (d, J=2.58 Hz, 1H), 5.93 (d, J=2.66 Hz, 1H), 5.08 (s, 2H), 1.93 (s, 3H), 1.77 (s, 3H). ES-HRMS m/z 420.0390 (M+H calcd for C20H17BrF2NO2, requires 420.0411).

Workup

  1. customA white precipitate was obtained which
  2. customwas isolated
  3. filtrationby filtering
  4. customfurther purified
  5. customby triturating with ether

Sources & evidence

ORD record
ord-9aa89381a27243899adf84168d0ed42b
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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