[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12]#[N:13].[H-].[Na+].[H][H].[CH3:18]I>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:18])[CH:7]=[C:6]2[C:12]#[N:13]
A solution of 5-methoxy-1H-indole-3-carbonitrile (550 mg) in dry tetrahydrofuran (50 ml) was treated with NaH (152 mg of a 55% dispersion in oil). The solution was stirred under a dry nitrogen atmosphere until the evolution of hydrogen ceased. Methyl iodide (0.45 mg) was then added and the reaction allowed to stir at room temperature for one hour. The solvent was then removed under reduced pressure and the residue taken up in dichloromethane (50 ml), washed with water (2×25 ml), dried (MgSO4), filtered, and evaporated to dryness under reduced pressure. The residue was recrystallised from absolute ethanol to afford the title compound as white prisms (480 mg); m.p. 105°-108° C.; δH (360 MHz, CDCl3) 3.84 (3H, s, OCH3), 3.87 (3H, s, NCH3), 6.98 (1H, dd, J=7.5, 1.0 Hz, H-6), 7.12 (1H, d, J=1.0 Hz, H-4), 7.31 (1H, d, J=7.5 Hz, H-7), 7.61 (1H, s, H-2); m/z 186 (M+ 100), 171 (90), 143 (80), 116 (20), 101 (15), 89 (15).
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