Methyl iodide → 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(2'-methyl-4-nitro-biphenyl-2-yl)-isobutyramide

HRID 1267515Notes

Reaction equation

HRID 1267515 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([C:13]([CH3:34])([CH3:33])[C:14]([NH:16][C:17]2[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:37][Si](C)(C)[N-][Si](C)(C)C.[K+].CI.C(OCC)(=O)C>CN(C)C=O.O1CCCC1>[F:1][C:2]([F:35])([F:36])[C:3]1[CH:4]=[C:5]([C:13]([CH3:34])([CH3:33])[C:14]([N:16]([CH3:37])[C:17]2[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])=[O:15])[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 18546488HCID 18546488, compound

Product 1

HCID 185464982-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(2'-methyl-4-nitro-biphenyl-2-yl)-isobutyramideYield 56%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.75 g (3.43 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-(2′-methyl-4-nitro-biphenyl-2-yl)-isobutyramide in 11 ml N,N-dimethylformamide under argon 4.1 ml (4.1 mmol) of 1 M potassium hexamethyldisilazide solution in tetrahydrofuran were added dropwise at 0°. Stirring was continued for 1 h at room temperature and the reaction mixture was cooled to 0° again. At this temperature 0.32 ml (5.14 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/hexane 1:1) to give 1.0 g (56%) 2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-N-(2′-methyl-4-nitro-biphenyl-2-yl)-isobutyramide as yellow crystals, MS (EI): 524 (M+).

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/hexane 1:1)

Sources & evidence

ORD record
ord-ef80920003f2464ea17b74c3cab1a1bb
Source dataset
uspto-grants-2003_04
Patent number
US06552088B2

Reaction notes

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