Sodium hydride → (5-Fluoro-2-oxo-3,4-dihydro-2H-quinoxalin-1-yl)acetic acid tert-butyl ester

HRID 558955Notes

Reaction equation

HRID 558955 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[NH:4][CH2:5][C:6](=[O:12])[NH:7]2.[H-].[Na+].Br[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>C1COCC1.[Cl-].[Na+].O>[C:20]([O:19][C:17](=[O:18])[CH2:16][N:7]1[C:8]2[C:3](=[C:2]([F:1])[CH:11]=[CH:10][CH:9]=2)[NH:4][CH2:5][C:6]1=[O:12])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 229128785-Fluoro-1,2,3,4-tetrahydroquinoxalin-2-one

Product 1

HCID 57470781(5-Fluoro-2-oxo-3,4-dihydro-2H-quinoxalin-1-yl)acetic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 5-fluoro-3,4-dihydro-1H-quinoxalin-2-one from Example B (475 mg, 2.86 mmol) in THF (10 ml) was added sodium hydride (60%, 115 mg, 2.86 mg) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature, stirred for 30 min and cooled in an ice/water bath. tert-Butyl bromoacetate (460 μl, 2.86 mmol) was added and the mixture was allowed to warm to room temperature slowly and stirred for 18 h. Brine was added and the mixture was evaporated in vacuo. The residue was partitioned between brine and EtOAc 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 white solid; yield 500 mg, 62%.

Workup

  1. temperaturewhile cooling in an ice/water bath
  2. temperaturecooled in an ice/water bath
  3. temperatureto warm to room temperature slowly
  4. stirringstirred for 18 h
  5. customthe mixture was evaporated in vacuo
  6. customThe residue was partitioned between brine and EtOAc
  7. customthe organic layer was dried
  8. customevaporated in vacuo
  9. customThe residue was purified by flash chromatography on silica (eluant EtOAc;pet. ether 40:60)
  10. customto give a white solid

Sources & evidence

ORD record
ord-e86dbc2a7fbb43f58fd2c09af5a23e3f
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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