Sodium Iodide → 1-[2-(tert-Butyldimethylsilanyloxy)ethyl]-5-fluoro-3,4-dihydro-1H-quinoxalin-2-one

HRID 558988Notes

Reaction equation

HRID 558988 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][CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].[I-].[Na+]>[Cl-].[Na+].O>[Si:19]([O:18][CH2:17][CH2:16][N:9]1[C:10]2[C:5](=[C:4]([F:3])[CH:13]=[CH:12][CH:11]=2)[NH:6][CH2:7][C:8]1=[O:14])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 229128785-Fluoro-1,2,3,4-tetrahydroquinoxalin-2-one

Product 1

HCID 670000521-[2-(tert-Butyldimethylsilanyloxy)ethyl]-5-fluoro-3,4-dihydro-1H-quinoxalin-2-one

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium hydride (60%, 128 mg, 3.2 mmol) was added to a solution of 5-fluoro-3,4-dihydro-1H-quinoxalin-2-one from Example B (530 mg, 3.2 mmol) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 10 min. (2-Bromoethoxy)-tert-butyldimethylsilane (789 mg, 3.3 mmol) and sodium iodide (495 mg, 3.3 mmol) were added and the mixture was stirred for 18 h. Brine was added and the mixture was evaporated in vacuo. The residue was taken up in EtOAc and brine, separated and the organic layer was dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc:pet.ether 40:60) to give a pale yellow solid: yield 600 mg, 58%.

Workup

  1. temperaturewhile cooling in an ice/water bath
  2. additionwere added
  3. customthe mixture was evaporated in vacuo
  4. custombrine, separated
  5. customthe organic layer was dried
  6. customevaporated in vacuo
  7. customThe residue was purified by flash chromatography on silica (eluant EtOAc:pet.ether 40:60)
  8. customto give a pale yellow solid

Sources & evidence

ORD record
ord-e129901dc95c43a0a99044a4205ebf58
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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