[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH3:14].C1COCC1>[Pd].CO>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH3:14]A solution of 1,2-dimethyl-5-nitro-1H-indole (500 mg) in 1:1 THF:methanol (10 mL) was treated with 10% palladium on carbon (100 mg), stirred under hydrogen (1 atm) for 1 hour, filtered through diatomaceous earth (Celite®), and concentrated. The crude product was used without further purification in the next step.
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