[S-:1][C:2]#[N:3].[K+].[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:15][C:14]=2[F:27])=[N:10][CH:11]=1.BrBr>C(O)(=O)C>[NH2:3][C:2]1[S:1][C:11]2[C:6]([N:5]=1)=[CH:7][CH:8]=[C:9]([O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[CH:15][C:14]=1[F:27])[N:10]=2To a solution of potassium thiocyanate (6.1 g, 62.6 mmol) in acetic acid (60 mL) was added a solution of tert-butyl {4-[(5-aminopyridin-2-yl)oxy]-3-fluorophenyl}carbamate (5.0 g, 15.7 mmol) in acetic acid (40 mL) at 0° C. A solution of bromine (3.25 g, 20.4 mmol) in acetic acid (20 mL) was added at 0° C., and the mixture was stirred at room temperature for 6 hr. Acetic acid was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate alone) to give the title compound (2.07 g, 35%).
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