Cesium carbonate → (NZ)-N-[3-[6-(trifluoromethyl)pyridin-3-yl]-1,3-thiazol-2-ylidene]pyrrolidine-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

In a 4 mL vial charged with a stir bar, N-1,3-thiazol-2-ylpyrrolidine-1-carboxamide (46 mg, 0.23 mmol, Example 32A) was added, followed by copper(I) trifluoromethanesulfonate benzene complex (30 mg, 0.05 mmol), 5-chloro-1,10-phenanthroline (23 mg, 0.09 mmol) and cesium carbonate (100 mg, 0.3 mmol). A loose cap with septum was placed on the vial and the vial was placed under vacuum in a vacuum oven for 30 minutes. The solid mixture was purged with nitrogen gas a couple of times. Then 5-bromo-2-(trifluoromethyl)pyridine (68 mg, 0.3 mmol) dissolved in 1-methyl-2-pyrrolidinone (1.0 mL) was added to the solid mixture. The vial was capped and placed on a heater/stirrer and heated to 120° C. overnight. Then a 1 mL solution of concentrated ammonium hydroxide/water (1:2) was added. The reaction was filtered and concentrated to dryness. The residue was purified by reverse phase HPLC (C18, gradient 10-95% acetonitrile/water/0.1% trifluoroacetic acid) to provide the title compound.

Provenance & Evidence