[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[C:9]([O:16][CH3:17])=[N:10][N:11]2[CH:15]=[CH:14][S:13][C:12]=12)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[Br:24]C(F)(F)C(F)(F)Br.[Cl-].[NH4+]>CCCCCCC.C(OCC)(=O)C.C(O)(=O)C.C(OCC)(=O)C.C1COCC1>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[C:9]([O:16][CH3:17])=[N:10][N:11]2[C:15]([Br:24])=[CH:14][S:13][C:12]=12)([CH3:4])([CH3:3])[CH3:2]
To a mixture of tert-butyl(6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl)carbamate (16.5 g, 61.4 mmol) and THF (410 mL) was added n-butyllithium (2.77 M n-hexane solution: 62.1 mL, 172 mmol) while stirring at −78° C. After stirring the mixture at −78° C. for 40 minutes, 1,2-dibromotetrafluoroethane (10.2 mL, 86 mmol) was added, and the mixture was stirred for two hours while warming to mom temperature. A saturated aqueous solution of ammonium chloride and ethyl acetate were added to the mixture, and then acetic acid was added so that the mixture became weakly acidic. After thoroughly shaking the mixture, the organic layer was separated and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=1/0 then 4/1) to obtain the title compound (14.3 g, 41.1 mmol).
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