[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=O)[CH:5]=[N:6][CH:7]=1.[OH:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][N:15]2[CH3:20].[C:21](#[N:25])[CH2:22][C:23]#[N:24].N1CCCCC1>C(O)C>[NH2:25][C:21]1[O:10][C:11]2[C:19]([CH:8]([C:4]3[CH:5]=[N:6][CH:7]=[C:2]([CH3:1])[CH:3]=3)[C:22]=1[C:23]#[N:24])=[CH:18][CH:17]=[C:16]1[N:15]([CH3:20])[CH:14]=[CH:13][C:12]=21To a solution of 5-methyl-pyridine-3-carbaldehyde (121 mg, 1 mmol) and 4-hydroxy-1-methyl-indole (146 mg, 0.99 mmol) in absolute ethanol (5 mL) at 0° C., was added malononitrile (67 mg, 1.01 mmol) and piperidine (0.1 mL). The clear solution was slowly warmed to room temperature and stirred overnight. The product was collected by vacuum filtration, washed with ethanol, and dried in vacuo as a yellow powder (269 mg, 86%). 1H NMR (CDCl3): 8.34 (d, J=2.1 Hz, 1H), 8.31 (dd, J=0.6, 2.1 Hz, 1H), 7.29 (m, 1H), 7.06 (d, J=3.0 Hz, 1H), 7.02 (dd, J=0.9, 8.4 Hz, 1H), 6.72 (d, J=8.4 Hz, 1H), 6.57 (dd, J=0.9, 3.0 Hz, 1H), 4.85 (s, 1H), 4.72 (brs, 2H), 3.77 (s, 3H), 2.27 (s, 3H).
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