C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=1[F:17].[C:18]([CH:20]1[CH2:22][CH:21]1[C:23](N(OC)C)=[O:24])#[N:19]>CCCCCC.C1COCC1.ClCCl>[F:17][C:8]1[CH:9]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:11]=[CH:12][C:7]=1[C:23]([CH:21]1[CH2:22][CH:20]1[C:18]#[N:19])=[O:24]2.6 ml (4.12 mmol) of a 1.6N solution of n-butyllithium in hexane were added dropwise to a solution of 1.00 g (4.12 mmol) of 1-bromo-2-fluoro-4-(trifluoromethyl)benzene in 8 ml of THF at −78° C., and the mixture was stirred for 0.5 h. Then, at −78° C., a solution of 423 mg (2.74 mmol) of the compound from Example 73A in 2 ml of THF was added, and the mixture was allowed to warm to RT and was stirred at RT for 2 h. It was diluted with dichloromethane, and the organic phase was washed with water and saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) to result in 206 mg (29% of theory) of the title compound.
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