Methyl iodide → HCID 11418800, compound

Participants

Reaction Steps

To a suspension of NaH (16.3 mg, 4190 mol, 60% dispersion in mineral oil) in THF (300 μL) at 0° C. was added a solution of 4-cyano-N-[2-ethyl-1-(1-phenyl-1H-pyrazol-5-yl)butyl]benzenesulfonamide (example 37, 140 mg, 340 μmol) in THF (600 EL). The reaction mixture was warmed to room temperature, and after 20 min iodomethane (45 μL, 714 μmol) was added. The mixture was allowed to stir overnight. TLC indicated that the reaction was not complete. Additional aliquots of NaH and iodomethane were added until the reaction was driven to completion. The mixture was then quenched with H2O and extracted with EtOAc twice. The organic extracts were dried (MgSO4) and concentrated. Column chromatography (EtOAc/hexanes, 1:1) provided 89 mg (57% yield) of the title compound as a glassy yellow solid. mp 37.8-54° C.; Mass Spectrum (ES): 481.1;

Provenance & Evidence