Cesium carbonate → 3-bromo-7-(2-chloro-3-(trifluoromethyl)benzyl)-6,7-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-8(5H)-one

Participants

Reaction Steps

To a slurry of 3-bromo-6,7-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-8(5H)-one (294 mg, 1.4 mmol) and cesium carbonate (1.32 g, 4.1 mmol) in DMF (10 mL) was added 1-(bromomethyl)-2-chloro-3-(trifluoromethyl)benzene (446 mg, 1.6 mmol). After 5 h, the reaction mixture was poured into ice cold brine (200 mL). The resulting precipitate was filtered and washed successively with water and ether to provide the product as a white solid (456 mg, 82%). MS (ESI): mass calcd. for C13H9BrClF3N4O, 408.0; m/z found, 409.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 7.82 (d, J=7.6 Hz, 1H), 7.77 (d, J=7.6 Hz, 1H), 7.55 (t, J=7.8 Hz, 1H), 4.85 (s, 2H), 4.36-4.24 (m, 2H), 3.99-3.83 (m, 2H).

Provenance & Evidence