[H-].[Na+].[NH2:3][C:4]1[N:5]([CH2:18][CH3:19])[C:6]2[C:11]([C:12]=1[C:13]#[N:14])=[CH:10][CH:9]=[C:8]([N+:15]([O-:17])=[O:16])[CH:7]=2.[C:20](Cl)(=[O:22])[CH3:21]>O1CCOCC1>[C:13]([C:12]1[C:11]2[C:6](=[CH:7][C:8]([N+:15]([O-:17])=[O:16])=[CH:9][CH:10]=2)[N:5]([CH2:18][CH3:19])[C:4]=1[NH:3][C:20](=[O:22])[CH3:21])#[N:14]Sodium hydride (44 mg, 1.10 mmol, 60% w/w in mineral oil) is washed with hexanes and suspended in 1,4-dioxane (3 mL). A solution of 2-amino-1-ethyl-6-nitro-1H-indole-3-carbonitrile (120 mg, 0.521 mmol), prepared in step B, above, in dioxane (2 mL) is added, and the resulting mixture is allowed to stir for 30 min. Then, acetyl chloride (45 μL, 0.63 mmol) is added by syringe, and the solution is stirred for an additional 12 h. The reaction is partitioned between water and EtOAc (20 mL each), and the organic phase is washed with brine. The aqueous phases are back-extracted in sequence with ethyl acetate, and the organic extracts are combined, dried over MgSO4, filtered and evaporated. The resulting solid is triturated with Et2O, collected by filtration and dried under vacuum to afford N-(3-cyano-1-ethyl-6-nitro-1H-indol-2-yl)-acetamide (100 mg, 71%), compound 25, as an off-white powder.
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