Cesium carbonate → HCID 59016003, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-[2-(4-Hydroxyphenyl)ethyl]-4-propyl-2-(4-trifluoromethylphenyl)-2,4-dihydro-[1,2,4]triazol-3-one (0.10 g, 0.26 mmol) and cesium carbonate (0.16 g, 0.49 mmol) in anhydrous DMF (2.5 mL) was added ethyl 2-bromoisobutyrate (81.1 mg, 60.6 □L, 0.42 mmol). The reaction mixture was heated to 75° C. overnight. More ethyl 2-bromoisobutyrate (30.3 □L) was added and the mixture was stirred at 110° C. overnight and ambient temperature over the weekend. The reaction mixture was quenched with water and extracted with ethyl acetate. The combined organic extracts were washed with 5% aqueous lithium chloride solution, water, brine, dried and evaporated. Chromatotron chromatography (gradient of ethyl acetate in hexanes) gave the pure compound (94 mg, 70.7%): 1HNMR (400 MHz, CDCl3) δ 8.14 (m, 2H), 7.65 (m, 2 H,), 7.10 (m, 2H), 6.80 (m, 2H), 4.23 (m, 2H), 3.53 (m, 2 H), 3.05 (m, 2H), 2.83 (m, 2H), 1.70 (m, 2H), 1.57 (s, 6 H), 1.26 (m, 6H); ESMS m/z (relative intensity) 506.1 (M+H+, 100).

Provenance & Evidence