(2Z)-3-Amino-2-butenenitrile → 2,6-Dimethyl-4-(3-methyl-1H-indazol-5-yl)-1,4-dihydropyridine-3,5-dicarbonitrile

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Reaction Steps

A mixture of 17.0 g (106.13 mmol) 3-methyl-1H-indazole-5-carbaldehyde, from Synthetic Preparation 10, and 17.86 g (217.57 mmol) 3-aminocrotononitrile were dissolved in 340 mL acetic acid and refluxed for 3 hours. After stirring overnight at room temperature the mixture was cooled with an ice bath, filtered and washed with a small amount of acetic acid. The product was dried under vacuum at 60° C. to afford 1,4-dihydro-2,6-dimethyl-4-(3-methyl-1H-indazol-5-yl)-3,5-pyridinedicarbonitrile (17.7 g, 57.6%) (Cpd. No. 81, Table 2). 1H-NMR (DMSO-D6): δ=12.68 (s, 1H), 9.51 (s, 1H), 7.53 (s, 1H), 7.49 (d, 1H), 7.27 (d, 1H), 4.50 (s, 1H), 2.49 (s, 3H), 2.05 (s, 6H) ppm. MS (ES+): 290.42 (M++1, 100%).

Provenance & Evidence