3-chloro-1-(4-fluorophenyl)pyrazin-2(1H)-one → 4-(4-Fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carbonitrile

HRID 2241373Notes

Reaction equation

HRID 2241373 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[CH:5]=[CH:6][N:7]=1.[C:16]([Cu])#[N:17]>CN1CCCC1=O>[F:14][C:11]1[CH:12]=[CH:13][C:8]([N:4]2[CH:5]=[CH:6][N:7]=[C:2]([C:16]#[N:17])[C:3]2=[O:15])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 672214163-chloro-1-(4-fluorophenyl)pyrazin-2(1H)-oneHCID 178418546HCID 178418546, compound

Product 1

HCID 673472474-(4-Fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carbonitrileYield 23.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-chloro-1-(4-fluorophenyl)pyrazin-2(1H)-one (3.52 g, 15.7 mmol), CuCN (2.81 g, 31.3 mmol) and N-methylpyrrolidone (30 mL) was heated for 5.5 hours at 150° C. while being stirred. The residue was triturated with hot CHCl3 and filtered over charcoal. The filtrate was evaporated and concentrated under reduced pressure. The residue was triturated with CH2Cl2 and the solution was concentrated. The crude was purified by silica gel flash column chromatography (3:1=CH2Cl2:Hexane then CH2Cl2) to afford 0.78 g (23%) of the desired product. LRMS (ESI pos) m/e 215.9 (M+1).

Workup

  1. customThe residue was triturated with hot CHCl3
  2. filtrationfiltered over charcoal
  3. customThe filtrate was evaporated
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was triturated with CH2Cl2
  6. concentrationthe solution was concentrated
  7. customThe crude was purified by silica gel flash column chromatography (3:1=CH2Cl2

Sources & evidence

ORD record
ord-c8b3c1b08ce84c42b3e8251050ee7707
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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