Tetrahydrofuran → 4-Acetyl-1-(4-fluorobenzyl)-3,4-dihydroquinoxalin-2(1H)-one

HRID 2109867Notes

Reaction equation

HRID 2109867 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6](=[O:14])[CH2:5]1)(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[F:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=1>CN(C=O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:35][C:34]2[CH:37]=[CH:38][C:31]([F:30])=[CH:32][CH:33]=2)[C:6](=[O:14])[CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 680214-Fluorobenzyl bromideHCID 2733832Lithium HexamethyldisilazideHCID 27708254-Acetyl-3,4-dihydroquinoxalin-2(1H)-one

Product 1

HCID 576346374-Acetyl-1-(4-fluorobenzyl)-3,4-dihydroquinoxalin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cold (0° C.) solution of 4-acetyl-3,4-dihydroquinoxalin-2(1H)-one (0.13 g, 0.68 mmol) in DMF (3.5 mL) under an atmosphere of nitrogen, a solution of lithium bis(trimethylsilyl)amide in THF (0.75 mL, 0.75 mmol) was added and stirred at the temperature for 30 min. The resultant solution was treated with 4-fluorobenzyl bromide (0.089 mL, 0.72 mmol), and stirred at room temperature for 3 hours. The product mixture was concentrated under vacuum, and the residue partitioned between aqueous HCl and ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 50% ethyl acetate in hexane. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. stirringstirred at room temperature for 3 hours
  2. concentrationThe product mixture was concentrated under vacuum
  3. customthe residue partitioned between aqueous HCl and ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-01a0e1e1091f430e9ed4ac589f2cfec7
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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