Methyl iodide → HCID 9805770, compound

HRID 1358616Notes

Reaction equation

HRID 1358616 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:13]([CH3:32])[C:14]([N:16]([CH3:31])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:23]([CH3:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:35][Si](C)(C)[N-][Si](C)(C)C.[K+].CI.C(OCC)(=O)C>CN(C)C=O>[F:1][C:2]([F:33])([F:34])[C:3]1[CH:4]=[C:5]([C:13]([CH3:35])([CH3:32])[C:14]([N:16]([CH3:31])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:23]([CH3:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:15])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 9913036HCID 9913036, compound

Product 1

HCID 9805770HCID 9805770, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 52 mg (0.11 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-[2-(methyl-phenyl-amino)-phenyl]-propionamide in 0.5 ml N,N-dimethylformamide at 0° C. were added 32 mg (0.16 mmol) potassium hexamethyldisilazide. Stirring was continued for 1 h at this temperature and 30 mg (0.16 mmol) methyl iodide were added. After stirring for 3 h at room temperature, ethyl acetate was added. The mixture was washed with brine, dried (magnesium sulfate) and evaporated. The solvent was removed in vacuo and the residue was purified by flash chromatography to give 54 mg (quantitative) of the title compound as colourless oil.

Workup

  1. additionwere added
  2. stirringAfter stirring for 3 h at room temperature
  3. washThe mixture was washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4b8e222c91d149eb89e0b4994c27e6ee
Source dataset
uspto-grants-2003_07
Patent number
US06596773B2

Reaction notes

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