C[O:2][C:3]([C:5]1[C:6](=[O:23])[N:7]([CH3:22])[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[CH:9][C:10]=1[CH3:11])=[O:4].[OH-].[Li+]>C1COCC1.CO>[CH3:22][N:7]1[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=2)=[CH:9][C:10]([CH3:11])=[C:5]([C:3]([OH:4])=[O:2])[C:6]1=[O:23]To a solution of 0.60 g (1.8 mmol) of 1,4-dimethyl-2-oxo-6-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid methyl ester 4.0 ml of THF/MeOH (1:1) was added 11.0 ml (11.0 mmol) of lithium hydroxide solution (1 molar in water) and the reaction mixture was then heated up to 60° C. After 7 hours, the solvents were evaporated and the residue poured into crashed ice, acidified with 2N HCl and extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 95:5) to give 0.53 g (94%) of the title compound as light yellow solid. MS: 310.1 (M−H−).
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