methyl 5-formyl-1H-indazole-3-carboxylate → 5-(3,5-dicyano-1,4-dihydro-2,6-dimethyl-4-pyridinyl)-1H-indazole-3-carboxylic acid methyl ester

Participants

Reaction Steps

A mixture of 5-formyl-1H-indazole-3-carboxylic acid methyl ester (92 mg, 0.45 mmol) and aminocrotononitrile (74 mg, 0.9 mmol) in HOAc (1 mL) was kept at 110° C. for 15 mins. After cooling to rt, the reaction mixture was diluted with EtOAc, washed with brine, dried, and concentrated. The crude product was purified by TLC to afford 5-(3,5-dicyano-1,4-dihydro-2,6-dimethyl-4-pyridinyl)-1H-indazole-3-carboxylic acid methyl ester (133 mg, 89%) (Cpd. No. 85, Table 2). 1H-NMR (400 MHz, DMSO-D6): δ=8.04 (s, 1H), 7.72 (s, 1H), 7.49 (d, 1H), 4.58 (s, 1H), 4.02 (s, 3H), 2.0 (s, 6H) ppm.

Provenance & Evidence