[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]#[N:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Br:23][C:24]1[CH:25]=[CH:26][C:27](F)=[N:28][CH:29]=1.O>O1CCCC1>[Br:23][C:24]1[CH:25]=[CH:26][C:27]([C:8]2([C:11]#[N:12])[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)=[N:28][CH:29]=1
After 1,4-dioxaspiro[4,5]decane-8-carbonitrile (2.5 g) was dissolved in tetrahydrofuran (8 ml), 1M tetrahydrofuran-solution of lithium bis(trimethylsilyl)amide (15 ml) was added at 0° C. and stirred for 30 minutes. 5-Bromo-2-fluoropyridine (2.64 g) was further added and stirred at room temperature for two hours. Water was added to the reaction solution, extracted with ethyl acetate and concentrated in vacuo. The residue was purified with silica gel chromatography (n-hexane/ethyl acetate) and the resulting solid was washed with n-hexane to give the titled compound (3.32 g).
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