Potassium Carbonate → HCID 22050158, compound

HRID 1831999Notes

Reaction equation

HRID 1831999 reaction equation
[Br:1][C:2]1[C:3](=[O:18])[N:4]([CH2:10][C:11]2[CH:16]=[N:15][C:14]([CH3:17])=[CH:13][N:12]=2)[C:5]([CH3:9])=[CH:6][C:7]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].[F:25][C:26]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:27]=1[CH2:28]Br>CC(N(C)C)=O>[Br:1][C:2]1[C:3](=[O:18])[N:4]([CH2:10][C:11]2[CH:16]=[N:15][C:14]([CH3:17])=[CH:13][N:12]=2)[C:5]([CH3:9])=[CH:6][C:7]=1[O:8][CH2:28][C:27]1[CH:30]=[CH:31][C:32]([F:34])=[CH:33][C:26]=1[F:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 54724159HCID 54724159, compound

Product 1

HCID 22050158HCID 22050158, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a mixture of 3-Bromo-4-hydroxy-6-methyl-1-[(5-methylpyrazin-2-yl)methyl]pyridin-2(1H)-one (0.45 g, 0.0015 mol), and potassium carbonate (0.25 g, 0.0018 mol) in dimethylacetamide (5.0 mL) was added 2,4 difluorobenzyl bromide (0.25 mL. 0.0019 mol)and stirred at room temperature under argon for 1 h. Dimethylacetamide was distilled in vacuo and the residue was partitioned between CH2Cl2 (20 mL) and water (20 mL). The organic phase was washed with water, dried (Na2SO4) and concentrated under reduced pressure. The resulting material was purified by flash chromatography (EtOAc/hexane 4:1 v/v) as the eluent. The appropriate fractions (m/z=451/453) were combined and concentrated under reduced pressure to give a white (0.25 g, 38%)solid. 1H NMR (CD3OD/400 MHz) δ 8.49 (s, 1H), 8.40 (s, 1H), 7.60 (m, 1H), 6.99 (m, 2H), 6.51 (s, 1H), 5.42 (s, 2H), 5.29 (s, 2H), 2.54 (s, 3H), and 2.50 (s, 3H); 19F NMR (CD3OD/400 MHz) δ−117.70 (m), and −116.09 (m); ES-HRMS m/z 436.0439 (M+H C19H17N3O2BrF2 requires 436.0467).

Workup

  1. distillationDimethylacetamide was distilled in vacuo
  2. customthe residue was partitioned between CH2Cl2 (20 mL) and water (20 mL)
  3. washThe organic phase was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting material was purified by flash chromatography (EtOAc/hexane 4:1 v/v) as the eluent
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-35ce79de41af46a3977d34e7c8e2cc8e
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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