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

Participants

Reaction Steps

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+).

Provenance & Evidence