1,2-Dichloroethane → 3-(6-amino-pyridin-3-yl)-N-(3-cyano-1H-indol-2-ylmethyl)-N-methyl-acrylamide

Participants

Reaction Steps

EDC (250 mg, 1.3 mmol) was added to a solution of (E)-3-(6-Amino-pyridin-3-yl)-acrylic acid (172 mg, 1.05 mmol), 2-methylaminomethyl-1H-indole-3-carbonitrile (186 mg, 1.0 mmol), HOBt H2O (135 mg, 1.0 mmol) and DIPEA (510 μL, 3.0 mmol) in dry DMF (4 mL). After 3 d of stirring, the mixture was diluted with water (50 mL) at 10° C. The resulting precipitate was filtered, washed with water and dried to afford the title compound (277 mg, 84%). 1H NMR (300 MHz, DMSO-d6, δ): 12.1 (m, 1H), 8.16 (s, 1H), 7.84 (s, 1H), 7.5 (m, 3H), 7.2 (m, 2H), 6.97 (m, 1H), 6.44 (s, 2H), 5.08 and 4.88 (rotamers, 2s, 2H), 3.22 and 2.96 (rotamers, 2s, 3H). MS (ESI): m/e 332 (M+H)+.

Provenance & Evidence