[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].C(=O)([O-])[O-].[Cs+].[Cs+].Cl.[Cl:14][C:15]1[C:16]([CH2:26]Cl)=[N:17][CH:18]=[C:19]([CH:25]=1)[C:20]([O:22]CC)=[O:21].[OH-].[Na+].Cl>CN(C=O)C.C1COCC1.O>[Cl:14][C:15]1[C:16]([CH2:26][O:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[N:17][CH:18]=[C:19]([CH:25]=1)[C:20]([OH:22])=[O:21]To a mixture of 2,2,2-trifluoroethanol (2.66 g, 26.6 mmol) and cesium carbonate (5.78 g, 17.7 mmol) in DMF (22 mL) is added ethyl 5-chloro-6-(chloromethyl)nicotinate hydrochloride (1.20 g, 4.44 mmol). After stirring at rt for 1 hour, 2 M aqueous sodium hydroxide solution (10 mL), water (20 mL), and THF (20 mL) are added to the mixture. After stirring at 60° C. for 2 hours, the mixture is acidified by 2 M hydrochloric acid (pH 4). The organic solvent is removed by evaporation, and the residual aqueous layer is extracted with EtOAc/hexane. The separated organic layer is dried over sodium sulfate, and after filtration, the filtrate is concentrated in vacuo to give 1.19 g (>99%) of the title compound as brown solid.
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