C([Li])CCC.[C:6](#[N:8])[CH3:7].Br[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])[N:11]=1>O1CCCC1>[C:17]1([CH3:24])[CH:18]=[C:19]([CH3:23])[CH:20]=[C:21]([CH3:22])[C:16]=1[C:12]1[N:11]=[C:10]([CH2:7][C:6]#[N:8])[CH:15]=[CH:14][CH:13]=1n-Butyllithium (2.5M, 19.1 mL, 47.8 mmol) was added to tetrahydrofuran (135 mL) and the solution was cooled to −78° C. Acetonitrile (2.5 mL, 47.8 mmol) was then added dropwise and the reaction stirred for 45 min. 2-Bromo-6-mesitylpyridine (2.00 g, 7.24 mmol) was added as a solution in 10 mL of tetrahydrofuran. The reaction continued to stir at −78° C. for 0.5 hr and was then warmed to room temperature for 1 h. The reaction was quenched with water and extracted with ethyl acetate, dried, and concentrated. Flash chromatography (20% ethyl acetate/hexanes) gave 0.70 g (41% yield) of the desired product as an orange oil.
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