[H-].[Na+].NC1NC2C(C=1C#N)=CC=C([N+]([O-])=[O:16])C=2.I[CH2:19][CH3:20].[NH2:21][C:22]1[N:23]([CH2:36][CH3:37])[C:24]2[C:29]([C:30]=1[C:31]#[N:32])=[CH:28][CH:27]=[C:26]([N+:33]([O-:35])=[O:34])[CH:25]=2>CCCCCC.CS(C)=O.CCOC(C)=O>[C:31]([C:30]1[C:29]2[C:24](=[CH:25][C:26]([N+:33]([O-:35])=[O:34])=[CH:27][CH:28]=2)[N:23]([CH2:36][CH3:37])[C:22]=1[NH:21][C:19](=[O:16])[CH3:20])#[N:32]Sodium hydride (42 mg, 1.05 mmol, 60% w/w suspension in mineral oil) was washed with hexane and taken up in dimethylsulfoxide (1 mL). A solution of 2-amino-6-nitro-1H-indole-3-carbonitrile, prepared in procedure 1T) in dimethylsulfoxide (1 mL) was added by syringe, and the resulting mixture was stirred for 20 min. Then, iodoethane (77 μL, 0.96 mmol) was added by syringe, and the mixture was stirred for 14 h. The reaction was then poured into EtOAc (50 mL), and this solution was washed with water (3×50 mL) and saturated brine (40 mL). The aqueous phases were back-extracted with EtOAc, and the organic extracts were combined, dried over Na2SO4, filtered and evaporated. The residual material was separated by column chromatography over silica gel (EtOAc/hexanes, 1/1) to afford first a small amount of a dialkylated analog, then the desired compound, 2-amino-1-ethyl-6-nitro-1H-indole-3-carbonitrile (114 mg, 52%), and finally unreacted starting material. The desired product was isolated as an orange powder.
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