Sodium Methoxide → 2-Amino-6,7-difluoro-3-methoxyquinoxaline

HRID 1907620Notes

Reaction equation

HRID 1907620 reaction equation
[NH2:1][C:2]1[C:11](Cl)=[N:10][C:9]2[C:4](=[CH:5][C:6]([F:14])=[C:7]([F:13])[CH:8]=2)[N:3]=1.[CH3:15][O-:16].[Na+]>O1CCCC1.CO>[NH2:1][C:2]1[C:11]([O:16][CH3:15])=[N:10][C:9]2[C:4](=[CH:5][C:6]([F:14])=[C:7]([F:13])[CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 866257803-Chloro-6,7-difluoroquinoxalin-2-amine

Product 1

HCID 692404792-Amino-6,7-difluoro-3-methoxyquinoxalineYield 95.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 2-amino-3-chloro-6,7-difluoroquinoxaline (610 mg, 2.83 mmol) dissolved in tetrahydrofuran (40 ml), 25 wt % sodium methoxide (6.12 g, 28.3 mmol) in methanol was added at room temperature and stirred further at room temperature for 1.5 hour. The resulting mixture was concentrated under the reduced pressure to remove the solvent. The product was extracted with ethyl acetate and the organic layer was washed with water and dried over MgSO4. After concentration under the reduced pressure, the crude product was purified by SiO2 column chromatography. Extraction of the residue with a n-hexane:ethyl acetate (2:1) mixture and concentration gave 570 mg of the titled compound (yield, 95%).

Workup

  1. concentrationThe resulting mixture was concentrated under the reduced pressure
  2. customto remove the solvent
  3. extractionThe product was extracted with ethyl acetate
  4. washthe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. concentrationAfter concentration under the reduced pressure
  7. customthe crude product was purified by SiO2 column chromatography
  8. extractionExtraction of the residue
  9. concentrationwith a n-hexane:ethyl acetate (2:1) mixture and concentration

Sources & evidence

ORD record
ord-02479bcdb48d49c9a8c989ff539a087c
Source dataset
uspto-grants-2013_12
Patent number
US08598173B2

Reaction notes

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