Acetic Acid → HCID 22050582, compound

HRID 1867004Notes

Reaction equation

HRID 1867004 reaction equation
[Br:1][C:2]1[C:3](=[O:19])[NH:4][C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].Cl[C:21]1[CH:26]=[N:25][CH:24]=[CH:23][N:22]=1.[H-].[Na+].[C:29](O)(=O)C>C1COCC1>[Br:1][C:2]1[C:3](=[O:19])[N:4]([CH2:29][C:21]2[CH:26]=[N:25][CH:24]=[CH:23][N:22]=2)[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 73277ChloropyrazineHCID 220504293-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one

Product 1

HCID 22050582HCID 22050582, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Bromo-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one (1.8 g, 0.0055 mol) and 2-chloropyrazine (0.8 g, 0.00625) were suspended in THF (25 mL), then added NaH (0.15 g, 0.0062 mol), KI (0.1 g) and the mixture was heated at 65° C. under argon atmosphere for 16 h. The reaction mixture was cooled, added acetic acid (0.5 mL) and concentrated to dryness under reduced pressure. The residue was stirred with a mixture of water (50 mL) and EtoAc (25 mL) and filtered the precipitate. It was washed with water, and acetonitrile an dried in vacuo to afford 1.7 g of light brown powder. 1H NMR (CD3OD/400 MHz) δ8.65 (d, 1H), δ 49 (m, 1H), 8.47 gm, 1H), 7.61 (˜q, 1H), 7.02 (m, 2H), 6.52 (s, 1H), 5.47 (s, 2H), 5.23 (s, 2H), and 2.53 (s, 3H);

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated to dryness under reduced pressure
  3. filtrationfiltered the precipitate
  4. washIt was washed with water, and acetonitrile
  5. customan dried in vacuo

Sources & evidence

ORD record
ord-28e163ba0e7947499d1ccd317bce1ae2
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

Loading…