Methyl iodide → (3R)-3-ethyl-7-fluoro-4-(4-methoxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-one

HRID 898214Notes

Reaction equation

HRID 898214 reaction equation
[CH2:1]([C@H:3]1[N:12]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:11]2[C:6](=[CH:7][C:8]([F:23])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:24])[CH3:2].[C:25](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[CH2:1]([C@H:3]1[N:12]([C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:11]2[C:6](=[CH:7][C:8]([F:23])=[CH:9][CH:10]=2)[N:5]([CH3:25])[C:4]1=[O:24])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 69224280(3R)-3-ethyl-7-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one

Product 1

HCID 69223654(3R)-3-ethyl-7-fluoro-4-(4-methoxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of (3R)-3-ethyl-7-fluoro-4-(4-methoxybenzoyl)-3,4-dihydroquinoxalin-2(1H)-one (0.21 g, 0.64 mmol) in acetone (5 mL) was added potassium carbonate (0.12 g, 0.87 mmol) followed by iodomethane (0.20 mL, 0.46 g, 3.2 mmol). The reaction vessel was flushed with nitrogen and sealed. The mixture was stirred at room temperature for 16 h, after which time additional iodomethane (0.20 mL, 0.46 g, 3.2 mmol) and potassium carbonate (0.11 g, 0.80 mmol) were added. Stirring was continued at 40° C. for an additional 20 h. The solvent was then evaporated, and the resulting residue was partitioned between water and ethyl acetate, separated, washed with water and dried over magnesium sulfate. Evaporation of the solvent under reduced pressure gave (3R)-3-ethyl-7-fluoro-4-(4-methoxybenzoyl)-1-methyl-3,4-dihydroquinoxalin-2(1H)-one (quantitative) as an oil that was used without further purification. MS (ESI) m/z 343 ([M+H]+); HRMS: calcd for C19H19FN2O3, 342.13804; found (ESI+), 343.14463.

Workup

  1. customThe reaction vessel was flushed with nitrogen
  2. customsealed
  3. stirringStirring
  4. waitwas continued at 40° C. for an additional 20 h
  5. customThe solvent was then evaporated
  6. customthe resulting residue was partitioned between water and ethyl acetate
  7. customseparated
  8. washwashed with water
  9. dry with materialdried over magnesium sulfate
  10. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-7812c716f9414b6abc4f9b23473837c2
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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