Sodium Iodide → 5-Fluoro-1-(2-methoxyethyl)-3,4-dihydro-1H-quinoxalin-2-one

HRID 558972Notes

Reaction equation

HRID 558972 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[NH:6][CH2:7][C:8](=[O:14])[NH:9]2.[CH3:15][O:16][CH2:17][CH2:18]Br.[I-].[Na+]>CN(C=O)C.[Cl-].[Na+].O>[F:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[NH:6][CH2:7][C:8](=[O:14])[N:9]2[CH2:18][CH2:17][O:16][CH3:15]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 229128785-Fluoro-1,2,3,4-tetrahydroquinoxalin-2-one

Product 1

HCID 231110975-Fluoro-1-(2-methoxyethyl)-3,4-dihydro-1H-quinoxalin-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium hydride (60%, 72 mg, 1.8 mmol) was added to a solution of 5-fluoro-3,4-dihydro-1H-quinoxalin-2-one from Example B (300 mg, 1.8 mmol) in DMF (6.0 ml) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 0.5 h. The mixture was cooled in an ice/water bath and 2-bromoethyl methyl ether (170 μl, 1.8 mmol) and sodium iodide (140 mg, 0.9 mmol) were added. The mixture was allowed to warm to room temperature and stirred for 18 h. The mixture was diluted with brine and evaporated in vacuo. The residue was partitioned between EtOAc and brine and separated. The organic phase was dried and evaporated. The residue was purified by flash chromatography (eluant EtOAc:pet.ether 55:45) to give a pale yellow gum; yield 200 mg, 50%.

Workup

  1. temperaturewhile cooling in an ice/water bath
  2. temperatureThe mixture was cooled in an ice/water bath
  3. temperatureto warm to room temperature
  4. stirringstirred for 18 h
  5. customevaporated in vacuo
  6. customThe residue was partitioned between EtOAc and brine
  7. customseparated
  8. customThe organic phase was dried
  9. customevaporated
  10. customThe residue was purified by flash chromatography (eluant EtOAc:pet.ether 55:45)
  11. customto give a pale yellow gum

Sources & evidence

ORD record
ord-8e266665f1d94f2bbdde020b8c1a4094
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

Loading…