Bromoacetonitrile → (5-Fluoro-2-oxo-3,4-dihydro-2H-quinoxalin-1-yl)acetonitrile

HRID 558967Notes

Reaction equation

HRID 558967 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.Br[CH2:16][C:17]#[N:18]>C1COCC1.[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[CH2:16][C:17]#[N:18]

Participants

6

Reactant 3

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 229128785-Fluoro-1,2,3,4-tetrahydroquinoxalin-2-one

Product 1

HCID 23111114(5-Fluoro-2-oxo-3,4-dihydro-2H-quinoxalin-1-yl)acetonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium hydride (60%, 84 mg, 2.1 mmol) was added to a solution of 5-fluoro-3,4-dihydro-1H-quinoxalin-2-one from Example B (316 mg, 1.9 mmol) in THF (2.0 ml) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 30 mins. Bromoacetonitrile (146 μl, 2.1 mmol) was added and the mixture was stirred for 18 h. Brine was added and the mixture evaporated in vacuo. The residue was portioned between EtOAc and water, separated and the organic phase was dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant 100% pet ether then EtOAc:pet. ether 20:80); yield 183 mg, 47%.

Workup

  1. temperaturewhile cooling in an ice/water bath
  2. stirringthe mixture was stirred for 18 h
  3. customthe mixture evaporated in vacuo
  4. customseparated
  5. customthe organic phase was dried
  6. customevaporated in vacuo
  7. customThe residue was purified by flash chromatography on silica (eluant 100% pet ether

Sources & evidence

ORD record
ord-e8749ed3e0804399b263c11da6114113
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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