[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[N:3]=1.[C-:10]#[N:11].[Na+]>CS(C)=O.C(OCC)(=O)C.O>[Br:1][C:2]1[N:3]=[C:4]([CH2:8][C:10]#[N:11])[CH:5]=[CH:6][CH:7]=1A solution of 2-bromo-6-(bromomethyl)pyridine (Example 190, Step 1) (5 g, 19.9 mmol) in dimethylsulfoxide (50 mL) was charged with sodium cyanide (2.93 g, 59.8 mmol). The reaction was heated to 50° C. overnight. Upon completion, the reaction was diluted with ethyl acetate (100 mL) and water (100 mL) and the layers were separated. The organic layer was then dried over sodium sulfate, filtered, concentrated, and purified by silica gel chromatography (hexane:ethyl acetate 7:3) followed by purification by reverse phase HPLC (10-100% acetonitrile/water+0.05% TFA modifier) to afford the title compound.
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