[Cl:1][C:2]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[CH:10]([CH:11]2[CH2:13][CH2:12]2)[CH2:9][NH:8][C:7](=[O:14])[C:6]1=[O:15].[C:24](=O)([O-])[O-].[Na+].[Na+].F[B-](F)(F)F.C([O+](CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[C:19]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[CH:10]([CH:11]2[CH2:12][CH2:13]2)[CH2:9][N:8]=[C:7]([O:14][CH3:24])[C:6]1=[O:15]To an ice cooled solution of Intermediate 5 (400 mg, 1.2 mmol) and sodium carbonate (2.5 g, 23 mmol) in DCM (45 mL) was added triethyloxonium tetrafluoroborate (1M in DCM, 5.8 mL, 5.8 mmol) dropwise. The ice bath was removed and the reaction was stirred at rt for 1.5 h. Water was added and the mixture was extracted with DCM (×3). The combined organic extracts were dried (Na2SO4), filtered, and concentrated to afford a yellow oil (432 mg, 100%), which was used directly without further purification. MS (ESI): mass calcd. for C17H18ClF3N2O2, 374.1; m/z found, 375.1 [M+H]+.
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