Potassium Carbonate → HCID 66916938, compound

Participants

Reaction Conditions

Reaction Steps

A round bottom flask was charged with (4-bromophenyl)(piperidine-4-yl)methanone (4.00 g, 14.9 mmol), 3-chlorophenyl boronic acid (3.26 g, 20.9 mmol, 1.4 eq), and Fibrecat 1029® (0.70 g, 0.448 mmol, 0.03 eq, Johnson Matthey). These solids were suspended in isopropanol (68 ml) and allowed to stir for five minutes. To this stirring solution was added potassium carbonate (6.18 g, 44.8 mmol, 3 eq.) dissolved in H2O (12 ml). The resulting solution was heated to 80° C. for 16 hours, at which time the reaction was deemed complete by LC/MS. The reaction mixture was filtered through a small bed of Celite® and the filtrate was concentrated to dryness. The resulting solids were dissolved in isopropyl acetate (100 ml) and washed with water (3×50 ml). The organics were cooled to 0° C., and to this stirring mixture was added slowly 6N HCl until solids crashed out of solution. The solids were filtered and dried for 16 hours at 50° C. in a vacuum oven to afford 2.89 g of compound 2 (72%) in >98% HPLC purity. MH+=300, 302 (about 3:1). Palladium: 4 ppm

Provenance & Evidence