Water → HCID 44477388, compound

HRID 589565Notes

Reaction equation

HRID 589565 reaction equation
Br[C:2]1[C:3](=[O:10])[N:4]([CH2:8][CH3:9])[CH:5]=[CH:6][N:7]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[C:3](=[O:10])[N:4]([CH2:8][CH3:9])[CH:5]=[CH:6][N:7]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 59085559HCID 59085559, compound

Product 1

HCID 44477388HCID 44477388, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 200 mg (0.98 mM) of 3-bromo-1-ethylpyrazin-2(1H)-one and 57 mg (0.05 mM) of palladium tetrakis triphenylphosphine in 4 ml of toluene were added, under nitrogen, 231.0 mg (1.48 mM) of 4-chlorophenylboronic acid and 2.9 ml of 2M sodium carbonate aqueous solution. The mixture was stirred for 3 h at reflux under nitrogen atmosphere, and then at room temperature overnight. Water was added and the mixture was extracted with ethyl acetate. The organic phase was separated, dried, over anhydrous sodium sulfate, and concentrated. The compound was purified through a silica plug, eluting with dichloromethane, which afforded 110 mg of 3-(4-chlorophenyl)-1-ethylpyrazin-2(1H)-one as a solid.

Workup

  1. temperatureat reflux under nitrogen atmosphere
  2. customat room temperature
  3. customovernight
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe organic phase was separated
  6. dry with materialdried, over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe compound was purified through a silica plug
  9. washeluting with dichloromethane, which

Sources & evidence

ORD record
ord-c63cfdbac5574468a370c65bcc7c70f5
Source dataset
uspto-grants-2016_01
Patent number
US09233937B2

Reaction notes

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