[CH:1](NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH:24]=[C:23]([C:25]#[C:26][C:27]3[CH:32]=[CH:31][N:30]=[C:29]([CH3:33])[CH:28]=3)[N:22]=[C:21]2[CH3:34])=[CH:16][CH:15]=1.CI>O1CCCC1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24]([CH3:1])=[C:23]([C:25]#[C:26][C:27]3[CH:32]=[CH:31][N:30]=[C:29]([CH3:33])[CH:28]=3)[N:22]=[C:21]2[CH3:34])=[CH:16][CH:15]=1Diisopropylamine (0.260 mg, 2.6 mmol) was dissolved in 5 mL dry tetrahydrofurane, n-butyllithium (1.6 mL, 1.6 M in hexane, 2.6 mmol) were added at −78° C. and the mixture was kept at −78° C. for 10 min. 4-[1-(4-Fluoro-phenyl)-2-methyl-1H-imidazol-4-ylethynyl]-2-methyl-pyridine (1) (500 mg, 1.72 mmol) in 5 mL dry tetrahydrofurane was added at −78° C. and stirring was continued for 45 min at this temperature. Methyl iodide (410 mg, 2.9 mmol) was added at −78° C. and the reaction mixture was slowly warmed to RT. The reaction mixture was quenched by addition of 50 mL water and extracted three times with diethylether (100 mL each). The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was purified by column chromatography on silica gel (methylenchloride/methanol 9:1) and the desired compound was obtained as a white solid (325 mg, 62%), MS: m/e=306.4 (M+H+).
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