Methyl iodide → HCID 67287768, compound

HRID 403300Notes

Reaction equation

HRID 403300 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][CH:16]=3)[NH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH3:26]I>CN(C=O)C.CCOC(C)=O.O>[F:23][C:2]([F:22])([F:1])[C:3]1[CH:4]=[C:5]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][CH:16]=3)[N:11]([CH3:26])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59626078HCID 59626078, compound

Product 1

HCID 67287768HCID 67287768, compoundYield 101.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 15d (300 mg, 0.78 mmol) in DMF (3 mL) was added NaH (60% in mineral oil, 68.9 mg, 1.72 mmol) at 0° C. The mixture was stirred at 0° C. for 30 min, then CH3I (0.053 mL, 0.86 mmol) was added and stirring continued at 0° C. for another 1 h. The resulting mixture was diluted with EtOAc and water. The organic layer was washed with brine and concentrated. The residue was recrystallized from heptane, filtered and the solid dried to give compound 15f (265 mg) as a light yellow solid. MS m/z (M+H+) 284.1.

Workup

  1. stirringstirring
  2. waitcontinued at 0° C. for another 1 h
  3. washThe organic layer was washed with brine
  4. concentrationconcentrated
  5. customThe residue was recrystallized from heptane
  6. filtrationfiltered
  7. customthe solid dried

Sources & evidence

ORD record
ord-f8a3592e38ee4a5bb4a50fe3235c7323
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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