Sodium Methoxide → 7-Fluoro-2-methoxyquinoxaline

HRID 1852286Notes

Reaction equation

HRID 1852286 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][C:6]([F:12])=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][O-:14].[Na+]>CO>[F:12][C:6]1[CH:5]=[C:4]2[C:9]([N:10]=[CH:11][C:2]([O:14][CH3:13])=[N:3]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 714639612-Chloro-7-fluoroquinoxaline

Product 1

HCID 866832797-Fluoro-2-methoxyquinoxalineYield 93.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-chloro-7-fluoroquinoxaline (0.1 g, 0.54 mmol) in methanol (15 ml) was added sodium methoxide (0.29 g, 0.54 mmol) at room temperature under nitrogen atmosphere. The reaction mass was heated at reflux for 3 h. The solvent was evaporated under reduced pressure and the residue was diluted with DCM and washed with water. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to get crude compound 7-fluoro-2-methoxyquinoxaline (0.09 g, 88% yield) as white solid. 1H NMR (400 MHz, CDCl3): δ ppm 8.41 (s, 1H), 8.01-7.98 (d, J=12 Hz, 1H), 7.49-7.46 (d, J=12 Hz, 2H), 7.34-7.3 (m, 1H), 4.09-4 (s, 3H); 19F NMR: δ ppm −108.99 (1F).

Workup

  1. temperatureThe reaction mass was heated
  2. temperatureat reflux for 3 h
  3. customThe solvent was evaporated under reduced pressure
  4. additionthe residue was diluted with DCM
  5. washwashed with water
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-e90c62d2fc80407caaa8bc0b052a2f95
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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