[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:11]1[C:16]([CH:17]=[CH:18][C:19]([OH:21])=[O:20])=[CH:15][CH:14]=[C:13]([C:22]([F:25])([F:24])[F:23])[N:12]=1>CN(C=O)C.CCOC(C)=O>[O:7]([C:11]1[C:16]([CH:17]=[CH:18][C:19]([OH:21])=[O:20])=[CH:15][CH:14]=[C:13]([C:22]([F:23])([F:25])[F:24])[N:12]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Phenol (57 mg, 0.60 mmol) and sodium hydride (32 mg, 0.8 mmol) were added in DMF (15 mL). The reaction mixture was stirred for 10 mins and then 3-(2-chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid (70 mg, 0.27 mmol) was added into the reaction mixture. The reaction mixture was diluted with EtOAc, and washed with water and brine. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Hex EtOAc=1/1) to give the title product (15 mg).
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