[Br:1][C:2]1[C:3]([C:16]2[S:17][CH2:18][C:19](O)([C:21]([F:24])([F:23])[F:22])[N:20]=2)=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.N1C(C)=CC=CC=1C>C(COC)OC>[Br:1][C:2]1[C:3]([C:16]2[S:17][CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[N:20]=2)=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1To a 2 L round bottom flask was charged tert-butyl 5-bromo-4-(4-hydroxy-4-(trifluoromethyl)-4,5-dihydrothiazol-2-yl)pyridin-2-ylcarbamate (Intermediate 86, 56.8 g, 128 mmol) and dimethoxyethane (800 mL). The reaction mixture was chilled in an ice-water bath, then trifluoroacetic anhydride (69 mL, 514 mmol) and 2,6-lutidine (133 mL, 1.15 mol) were added simultaneously over 1 h. An orange/yellow solution which resulted was allowed to stir in the ice-water bath for 30 min, then the solution was warmed to room temperature. The orange solution was concentrated under reduced pressure to dryness, and the resulting residue was triturated with methanol. The solid was collected by filtration and washed with more methanol, dried under vacuum overnight, yielding 49 g of white solid.
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