Potassium Cyanide → 1H-Indole-3-acetonitrile, 4-nitro-

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[C-:1]#[N:2].[K+].CN(C)[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N+:16]([O-:18])=[O:17])[NH:9][CH:8]=1>O.CN(C=O)C>[N+:16]([C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[C:7]([CH2:6][C:1]#[N:2])=[CH:8][NH:9]2)([O-:18])=[O:17]

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Potassium cyanide (9.20 g, 141 mmol) in H2O (80 mL) was added to a solution of N,N-dimethyl-1-(4-nitro-1H-indol-3-yl)methanamine from Step A (3.10 g, 14.1 mmol) in DMF (80 mL) and the mixture was heated at reflux for 1 h, then cooled to ambient temperature and partitioned between H2O (200 mL) and EtOAc (400 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 0:100, to give the title compound. MS: m/z=265 (M+Na+CH3CN).