C([Li])CCC.[CH:6]([NH:9]C(C)C)(C)C.[Br:13][C:14]1[N:19]=[C:18](CC#N)[CH:17]=[CH:16][CH:15]=1.[CH3:23]I.C(O[CH2:29][CH3:30])(=O)C>C1COCC1.O>[Br:13][C:14]1[N:19]=[C:18]([C:29]([CH3:30])([CH3:23])[C:6]#[N:9])[CH:17]=[CH:16][CH:15]=1n-Butyllithium (6.48 ml, 10.4 mmol) was added to a cooled (0° C.) solution of diisopropylamine (1.48 ml, 10.4 mmol) in THF (10 mL). The reaction was maintained at 0° C. for 30 minutes, at which time it was cooled to −78° C. and a solution of (6-bromopyridin-2-yl)acetonitrile (Example 235, Step 1) (930 mg, 4.71 mmol) in THF (10 mL) was added dropwise. The reaction was then maintained at −78° C. for 1 hour and then methyl iodide (0.65 ml, 10.4 mmol) was added. The reaction was allowed warm to room temperature slowly overnight. The mixture was then diluted with water and ethyl acetate and the layers were separated. The organic layer was then dried over sodium sulfate, filtered and concentrated to yield the title compound.
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