Water → 1-[2-(1,3-Dioxolan-2-yl)ethyl]-6,7-difluoroquinoxalin-2(1H)one

HRID 1847083Notes

Reaction equation

HRID 1847083 reaction equation
[H-].[Li+].[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[F:14])[NH:10][C:9](=[O:15])[CH:8]=[N:7]2.Br[CH2:17][CH2:18][CH:19]1[O:23][CH2:22][CH2:21][O:20]1.O>CN(C)C=O>[O:20]1[CH2:21][CH2:22][O:23][CH:19]1[CH2:18][CH2:17][N:10]1[C:11]2[C:6](=[CH:5][C:4]([F:3])=[C:13]([F:14])[CH:12]=2)[N:7]=[CH:8][C:9]1=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 62714Lithium hydrideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 63243396,7-Difluoro-1,2-dihydroquinoxalin-2-one

Product 1

HCID 867250061-[2-(1,3-Dioxolan-2-yl)ethyl]-6,7-difluoroquinoxalin-2(1H)oneYield 39.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Lithium hydride (52 mg, 6.5 mmol) was added to a solution of 6,7-difluoroquinoxalin-2(1H)one (1 g, 5.4 mmol) in N,N-dimethylformamide (10 ml) under cooling on ice and the reaction mixture was stirred at room temperature for 30 minutes. The mixture was cooled on ice again, a solution of 2-(2-bromoethyl)-1,3-dioxolane (0.8 ml, 6.5 mmol) in N,N-dimethylformamide (2 ml) was gradually added thereto and the obtained mixture was stirred for 4 hours. Water was gradually added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 0.6 g (39%) of the title compound.

Workup

  1. temperatureunder cooling on ice
  2. temperatureThe mixture was cooled on ice again
  3. stirringthe obtained mixture was stirred for 4 hours
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f22b316797924e9795d6a22d2297d046
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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