C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=2)[C:11]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)=[CH:10]1.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[C:25]([C:24]1[CH:23]=[CH:22][C:21]([C:11]2[C:12]3[C:17](=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=3)[N:9]([NH:8][C:5](=[O:7])[CH3:6])[CH:10]=2)=[CH:28][CH:27]=1)#[N:26]Add acetic anhydride (214 mg, 2.1 mmol) to a mixture of 4-(1-Amino-6-nitro-1H-indol-3-yl)-benzonitrile (400 mg, 1.4 mmol) and di-isopropylethylamine (194 mg, 2.1 mmol) and N,N-dimethylaminopyridine (2 mg) in DMF (20 mL) and stir for 3 h. Add additional acetic anhydride (214 mg, 2.1 mmol) and di-isopropylethylamine (194 mg, 2.1 mmol) and stir overnight. Dilute the mixture with water and extract with EtOAc. Wash the combined extracts with water and brine, and dry over MgSO4. Purify the crude residue using silica gel chromatography to give 170 mg (38% yield) of N-[3-(4-Cyano-phenyl)-6-nitro-indol-1-yl]-acetamide.
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