Methanol → HCID 59866236, compound

HRID 45566Notes

Reaction equation

HRID 45566 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[N:6][CH:5]=[CH:4][N:3]=1.[CH3:15][O-:16].[Na+].CO>O>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]2[C:2]([O:16][CH3:15])=[N:3][CH:4]=[CH:5][N:6]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 598662582-Chloro-3-(4-fluorophenyl)pyrazine

Product 1

HCID 59866236HCID 59866236, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Next, 3.87 g of 2-chloro-3-(4-fluorophenyl)pyrazine, 2.01 g of sodium methoxide, and 30 mL of methanol were put in a three-neck flask equipped with a reflux pipe, and reacted by being heated and refluxed under a nitrogen atmosphere for three hours. After the reaction, the reaction solution was cooled down to room temperature, water was added thereto, and an organic layer was extracted with dichloromethane. The obtained organic layer was washed with a saturated saline and water, and dried with magnesium sulfate. Then, magnesium sulfate was removed by filtration and the solvent was distilled off, so that 2-(4-fluorophenyl)-3-methoxypyrazine was obtained (milky white powder, yield: 96%). A synthetic scheme of Step 2 is shown in the following (a1-2).

Workup

  1. customequipped with a reflux pipe
  2. customreacted
  3. temperatureby being heated
  4. temperaturerefluxed under a nitrogen atmosphere for three hours
  5. customAfter the reaction
  6. extractionan organic layer was extracted with dichloromethane
  7. washThe obtained organic layer was washed with a saturated saline and water
  8. dry with materialdried with magnesium sulfate
  9. customThen, magnesium sulfate was removed by filtration
  10. distillationthe solvent was distilled off, so that 2-(4-fluorophenyl)-3-methoxypyrazine
  11. customwas obtained (milky white powder, yield: 96%)

Sources & evidence

ORD record
ord-dcce1524f3bc4034bb359a74dbbce28f
Source dataset
uspto-grants-2013_09
Patent number
US08541574B2

Reaction notes

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