[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].[ClH:13]>[Pd].CO>[ClH:13].[ClH:13].[NH2:2][CH2:1][C:3]1[C:4]([CH3:12])=[C:5]2[C:9](=[N:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2A suspension of 5-cyano-4-methyl-7-azaindole (48 mg, 0.31 mmol) and 10% palladium on carbon (25 mg) in methanol (10 mL) and concentrated HCl (0.5 mL) was shaken on a Parr apparatus under hydrogen (50 psi) for 6 h. The mixture was filtered through celite and evaporated in vacuo. The residue was dissolved in a minimum volume of methanol, ether was added and the solids collected by filtration to give the title compound as a pale yellow solid:
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