[Br:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]#[N:10])[CH:5]=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Br[CH2:22][CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>C1COCC1.O>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([CH2:22][CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[C:9]#[N:10])[CH:5]=[CH:4][CH:3]=1(6-Bromopyridin-2-yl)acetonitrile (Example 235, Step 1) (500 mg, 2.54 mmol) was dissolved in THF (10 mL) and cooled to −78° C. LHMDS (1.0 M in THF, 3.05 ml, 3.05 mmol) was added dropwise, and the solution was maintained at −78° C. for 20 minutes. A solution of (2-bromoethoxy)-tert-butyldimethylsilane (600 μL, 2.79 mmol) in THF (5.0 mL) was added dropwise over 5 minutes. The resulting mixture was maintained at −78° C. for 2 hours and warmed to room temperature overnight. The solution was then diluted with water and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated. Silica gel chromatography (0-15% EtOAc/hexanes) afforded the title compound as a colorless oil.
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