[Br:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4]([NH:11][C:12](=O)[C:13](F)(F)F)[CH:3]=1.ICC.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[K+].[K+]>O.CCOC(C)=O.CN(C=O)C>[Br:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[C:4]([NH:11][CH2:12][CH3:13])[CH:3]=1A mixture of methyl 5-bromo-3-[(trifluoroacetyl)amino]thiophene-2-carboxylate (3.18 g, 9.58 mmol), iodoethane (3.8 mL, 47.9 mmol), cesium carbonate (7.80 g, 24.0 mmol) and DMF (10 mL) was stirred at 70° C. for 3 h. Then, water and EtOAc were added to quench the reaction. The organic materials were extracted with EtOAc. The combined extracts were washed with water and brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was dissolved in MeOH (15 mL). To the solution were added potassium carbonate (3.97 g, 28.7 mmol) and water (10 mL). The mixture was stirred at room temperature for 2 h. After removal of the solvent at reduced pressure, the organic materials were extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, hexane to 90:10 hexane/EtOAc) to give the title compound (2.46 g, 97%) as a light green oil:
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