Br[C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[C:7]([Cl:13])[N:8]=[CH:9]2)=[CH:4][CH:3]=1.[C:14]([Cu])#[N:15].CN(C=O)C>C(Cl)Cl>[Cl:13][C:7]1[N:8]=[CH:9][C:10]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[C:2]([C:14]#[N:15])[C:11]=2[CH3:12]To a flask containing a stir bar was added 7-Bromo-3-chloro-8-methylisoquinoline (0.63 g, 2.4 mmol), CuCN (0.33 g, 3.7 mmol), and DMF (10 mL). The mixture was then refluxed at 150° C. overnight. When the reaction was complete, as evidenced by LC analysis, the reaction flask was taken out of the oil bath and cooled to room temperature. To the mixture was then poured DCM (20 mL) and a precipitate formed immediately, which was filtered, re-dissolved in DCM, adsorbed into silica gel and purified by silica gel column chromatography (Hexanes:DCM→1:1) to provide the title product. LC/MS (IE, m/z): [M+1]+=203.
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