Methyl iodide → 1-(2-Bromo-5-fluorophenyl)-4-methyl-1H-1,2,4-triazol-5(4H)-one

Participants

Reaction Steps

To a stirred suspension of sodium hydride (0.124 g of a 60% dispersion in mineral oil, 3.09 mmol) in DMF (5 mL) was added a solution of 1-(2-bromo-5-fluorophenyl)-1H-1,2,4-triazol-5(4H)-one (0.725 g, 2.81 mmol) in DMF (5 mL) at 0° C. The resulting mixture was stirred 45 min at room temperature followed by the addition of iodomethane (0.23 mL, 3.65 mmol). The mixture was stirred at room temperature for 2 h and then poured onto saturated aqueous NH4Cl. The product was extracted with EtOAc, washed with water (3×), brine, dried over Na2SO4 and filtered. The residue was purified with a Biotage column chromatography system on silica gel with hexanes:ethyl acetate (3:7) gradient as the eluent to afford the title compound as a white solid (0.508 g, 66% yield): 1H NMR (400 MHz, CDCl3) δ 7.65 (1H, dd, J=9.0, 5.4 Hz), 7.56 (1H, s), 7.20 (1H, dd, J=8.6, 3.0 Hz), 7.04 (1H, ddd, J=8.9, 7.6, 2.9 Hz), 3.39 (3H, s); LCMS (ESI, M+H+) m/z 272-274.

Provenance & Evidence