Methyl iodide → HCID 18546484, compound

HRID 1267518Notes

Reaction equation

HRID 1267518 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:33])[C:16]([C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=1)([CH3:18])[CH3:17].CI.[C:36](OCC)(=O)C>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]([CH3:36])[C:15](=[O:33])[C:16]([C:19]1[CH:20]=[C:21]([C:29]([F:30])([F:31])[F:32])[CH:22]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:24]=1)([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 18546505HCID 18546505, compound

Product 1

HCID 18546484HCID 18546484, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 151 mg (0.32 mmol) N-(2′-amino-biphenyl-2-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-isobutyramide in 1 ml N,N-dimethylformamide under argon 130 mg (0.65 mmol) potassium hexamethyldisilazide were added at 0°. Stirring was continued for 1 h at room temperature and the reaction mixture was cooled to 0° again. At this temperature, 115 mg (0.81 mmol) methyl iodide were added. After stirring for 3 hrs at room temperature, ethyl acetate was added and the organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was purified by chromatography (SiO2, ethyl acetate/CH2Cl2 1:1) to give 56 mg (36%) N-(2′-amino-biphenyl-2-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide as colorless oil, MS (ISP): 481.1 (M+H)+.

Workup

  1. temperaturethe reaction mixture was cooled to 0° again
  2. stirringAfter stirring for 3 hrs at room temperature
  3. washthe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by chromatography (SiO2, ethyl acetate/CH2Cl2 1:1)

Sources & evidence

ORD record
ord-9d3047957daa49c1b1404c77b6327747
Source dataset
uspto-grants-2003_04
Patent number
US06552088B2

Reaction notes

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