[N:1]([CH:4]1[CH2:10][CH2:9][C:8]2[C:11]([F:15])=[CH:12][CH:13]=[CH:14][C:7]=2[NH:6][C:5]1=[O:16])=[N+:2]=[N-:3].C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:29][C:30]([F:33])([F:32])[F:31])(=O)=O>CN(C=O)C.O.CCOC(C)=O>[N:1]([CH:4]1[CH2:10][CH2:9][C:8]2[C:11]([F:15])=[CH:12][CH:13]=[CH:14][C:7]=2[N:6]([CH2:29][C:30]([F:33])([F:32])[F:31])[C:5]1=[O:16])=[N+:2]=[N-:3]
3-Azido-6-fluoro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (2.25 g, 10.22 mmol), cesium carbonate (4.65 g, 14.30 mmol), and 2,2,2-trifluoroethyl trifluoromethanesulfonate (2.67 mL, 18.39 mmol) in DMF (34.1 mL) heated to 40° C. for 1 hour. The reaction 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 yield the crude product. This material was chromatographed on silica gel (0-80% EtOAc in hexanes) to yield 2.534 g of 3-azido-6-fluoro-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one as an orange/brown solid.
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