Methyl iodide → HCID 57671765, compound

HRID 871987Notes

Reaction equation

HRID 871987 reaction equation
[C:1]([O:9][CH2:10][C:11]1[C:12]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[O:31][CH3:32])=[CH:13][CH:14]=[C:15]2[C:20]=1[NH:19][C:18](=[O:21])[C:17]([CH3:23])([CH3:22])[NH:16]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:35](=O)([O-])[O-]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:9][CH2:10][C:11]1[C:12]([C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[O:31][CH3:32])=[CH:13][CH:14]=[C:15]2[C:20]=1[N:19]([CH3:35])[C:18](=[O:21])[C:17]([CH3:23])([CH3:22])[NH:16]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 19660Carbonate IonHCID 57671844HCID 57671844, compound

Product 1

HCID 57671765HCID 57671765, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8-benzoyloxymethyl-7-(5-fluoro-2-methoxyphenyl)-3,3-dimethyl-3,4-dihydro-1H-quinoxalin-2-one (Compound No. 1-3, 42.9 mg, 0.099 mmol), methyliodide (30.7 μL, 0.49 mmol), and cessium carbonate (89.0 mg, 0.27 mmol) was suspended in anhydrous N,N-dimethylformamide (1 mL) and stirred at room temperature for 1.5 hours. The reaction mixture was diluted with ethyl acetate (100 mL). The mixture was washed with water (100 mL) and saturated brine (50 mL) successively, 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 compound (35.0 mg) as a colorless amorphous product. (Yield 79%)

Workup

  1. washThe mixture was washed with water (100 mL) and saturated brine (50 mL) successively
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-556fb0c4181c4fceb638740ce13bc3ab
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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