Cesium carbonate → 6-fluoro-3-(4-{4-[(2-methylpyridin-3-yl)oxy]phenyl}-1H-1,2,3-triazol-1-yl)-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Participants

Reaction Steps

3-[4-(4-Bromophenyl)-1H-1,2,3-triazol-1-yl]-6-fluoro-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (150 mg, 0.310 mmol), cesium carbonate (202 mg, 0.621 mmol), 3-hydroxy-2-methylpyridine (67.7 mg, 0.621 mmol), cuprous chloride (915.36 mg, 0.155 mmol), 2,2,6,6-tetramethyl-3,5-heptanedione (14.30 mg, 0.078 mmol) in NMP (1.55 mL) in a sealed microwave vial was heated to 120° C. overnight in an oil bath. The reaction vessel was allowed to cool before water was added to dilute the mixture; EtOAc was then added to extract the product. The organic phase was separated and washed with water (2×) and brine (1×) before being dried with Na2SO4 and evaporated to afford an oil. This material was chromatographed on silica (0-80% EtOAc in hexanes to yield 68.4 mg as a solid.

Provenance & Evidence