[C:1]([C:3]1[C:4]([CH3:12])=[C:5]2[C:9](=[N:10][CH:11]=1)[NH:8][CH2:7][CH2:6]2)#[N:2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:1]([C:3]1[C:4]([CH3:12])=[C:5]2[C:9](=[N:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#[N:2]A mixture of 5-cyano-4-methyl-7-azaindoline (52 mg, 0.33 mmol) and manganese dioxide (130 mg, 1.5 mmol) in chloroform (10 mL) was stirred for 16 h and then was filtered through celite, washing through with chloroform followed by methanol. The filtrate was evaporated in vacuo to give the title compound as a tan solid:
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