Water → HCID 86725012, compound

HRID 1847088Notes

Reaction equation

HRID 1847088 reaction equation
[H-].[Li+].[F:3][C:4]1[CH:13]=[C:12]2[C:7]([N:8]=[CH:9][C:10](=[O:14])[NH:11]2)=[CH:6][CH:5]=1.Br[CH2:16][CH2:17][CH:18]1[O:22][CH2:21][CH2:20][O:19]1.O>CN(C)C=O>[O:19]1[CH2:20][CH2:21][O:22][CH:18]1[CH2:17][CH2:16][N:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([F:3])[CH:13]=2)[N:8]=[CH:9][C:10]1=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 62714Lithium hydrideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 217275347-fluoroquinoxalin-2(1H)-one

Product 1

HCID 86725012HCID 86725012, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Lithium hydride (88 mg, 011 mmol) was added to a solution of 7-fluoroquinoxalin-2(1H)one (1.3 g, 7.8 mmol) in N,N-dimethylformamide (40 ml) under cooling on ice and the mixture was stirred at room temperature for 30 minutes. The mixture was cooled on ice and 2-(2-bromoethyl)-1,3-dioxolane (1.33 ml, 11 mmol) was added thereto. The obtained mixture was stirred at room temperature for 24 hours, water was then gradually added thereto and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (dichloromethane/methanol) to yield 0.6 g (29%) of the title compound.

Workup

  1. temperatureunder cooling on ice
  2. additionwas added
  3. stirringThe obtained mixture was stirred at room temperature for 24 hours
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained crude product
  8. customwas purified by silica gel column chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-4377bf453226494d9f1e44aa5a04d88a
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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