Cesium carbonate → HCID 68351647, compound

Participants

Reaction Steps

A solution of 3-(4-bromophenyl)-1H-pyrazole (302 g, 1.35 mol), cyclopropylboronic acid (233 g, 2.71 mol), copper(II) acetate (246 g, 1.35 mol), 4-(dimethylamino)pyridine (662 g, 5.42 mol), cesium carbonate (1103 g, 3.39 mol), and 1,4-dioxane (8 L) was stirred at 90° C. for 36 h. The reaction mixture was cooled to room temperature before being filtered through Celite™, which was washed with EtOAc (4 L). The filtrate was acidified to pH 5 with 2 N HCl. The aqueous layer was extracted with EtOAc (12 L). The organic layers were combined, washed with brine, dried over MgSO4, filtered, and evaporated under reduced pressure. The resulting residue was purified on an ISCO 1500 g column eluting with a 0-20% EtOAc/Heptane gradient to afford the title compound. LC-MS: calculated for C12H11BrN2 262.01, 264.01, observed m/e: 263.04, 265.06 (M+H)+ (Rt 1.19/2 min).

Provenance & Evidence