C(=O)([O-])[O-].[K+].[K+].[N+:7]([C:10]1[CH:18]=[C:17]2[C:13]([C:14]([CH2:19][C:20]#[N:21])=[CH:15][NH:16]2)=[CH:12][CH:11]=1)([O-:9])=[O:8].[CH3:22]I.O>CN(C)C=O>[CH3:22][N:16]1[C:17]2[C:13](=[CH:12][CH:11]=[C:10]([N+:7]([O-:9])=[O:8])[CH:18]=2)[C:14]([CH2:19][C:20]#[N:21])=[CH:15]165.5 g (0.474 mol) of powdered potassium carbonate was added to a solution of 28.9 g (0.143 mol) of (6-nitro-1H-indol-3,yl)-acetonitrile (13) from Step C above in 230 ml of dimethylformamide at room temperature. The suspension was stirred for 40 minutes then 25.48 g (0.179 mol) of methyl iodide was added dropwise over 65 minutes. After stirring at room temperature over night the reaction mixture was cooled and poured into a total of 600 ml of water. The precipitate was filtered, washed with a little water and dried on phosphor anhydride until reaching constant weight. The procedure yielded 30.4 g (95.4%) of (1-methyl-6-nitro-1H-indol-3-yl)acetonitrile (14), which was used without further purification.
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