Br[C:2]1[C:3]([CH3:11])=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.[Cu][C:13]#[N:14]>CN(C=O)C>[C:13]([C:2]1[C:3]([CH3:11])=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2)#[N:14]A stirred mixture of 5-bromo-4-methyl-7-azaindoline (270 mg, 1.27 mmol) and copper (I) cyanide (135 mg, 1.5 mmol) in DMF (0.3 mL) was heated to 180° C. for 4 h. The reaction mixture was cooled and partitioned between 5% potassium cyanide solution and ethyl acetate. The organic layer was dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash column chromatography (50% ethyl acetate/hexanes) to give the title compound:
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