Methyl iodide → 7-Bromo-8-methoxycarbonyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 1038474Notes

Reaction equation

HRID 1038474 reaction equation
[Br:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[C:5]([NH:6][C:7]([CH3:18])([CH3:17])[C:8](=[O:16])[NH:9]2)=[CH:4][CH:3]=1.CI.[C:21](=O)([O-])[O-].C(OCC)(=O)C>CN(C)C=O.O>[Br:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[C:5]([NH:6][C:7]([CH3:18])([CH3:17])[C:8](=[O:16])[N:9]2[CH3:21])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 19660Carbonate IonHCID 24780709Methyl 6-bromo-2,2-dimethyl-3-oxo-1,2,3,4-tetrahydroquinoxaline-5-carboxylate

Product 1

HCID 247809997-Bromo-8-methoxycarbonyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-oneYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-bromo-8-methoxycarbonyl-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 1, 102 mg, 0.326 mmol), methyl iodide (100 μL, 1.60 mmol), and cessium carbonate (272 mg, 0.835 mmol) was suspended in anhydrous N,N-dimethylformamide (5 mL) and stirred at room temperature for 2 hours. Ethyl acetate (25 mL) and water (25 mL) were added to the reaction mixture and partitioned. The organic layer was washed with saturated brine (20 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (86.0 mg) as a pale yellow solid. (Yield 83%)

Workup

  1. custompartitioned
  2. washThe organic layer was washed with saturated brine (20 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-7355dd23b7df4b1bbba0a5f362a5715c
Source dataset
uspto-grants-2013_10
Patent number
US08551991B2

Reaction notes

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