Dimethylformamide → 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

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Reaction Steps

1-Bromo-4-ethynylbenzene (271 mg, 1.499 mmol), cupric sulfate (65.2 mg, 0.409 mmol), sodium ascorbate (108 mg, 0.545 mmol), and 3-azido-6-fluoro-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (300 mg, 1.362 mmol) in 6.6 mL of a 1:1:1 solution of DMF:EtOH:H2O was stirred for 25 mins. The mixture was diluted with water before EtOAc was 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 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 (495.1 mg) as a solid.

Provenance & Evidence