1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-amine → methyl 1-(3-chlorophenyl)-6-(furan-2-yl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Participants

Reaction Steps

(see, e.g., Volochnyuk, D. M., et al., J Comb Chem 2010, 12, 510-7). A solution of 22 (306 mg, 1.47 mmol) and 20 (295 mg, 1.50 mmol) in glacial AcOH (10 mL) was heated to reflux for 3 h. When the reaction mixture was cooled down to room temperature, yellow precipitates formed which were filtered and washed with H2O. Filtercake was placed in a vacuum oven to give the title compound (470 mg, 87%) as a yellow solid. 1H NMR (500 MHz, CDCl3) δ 8.48 (s, 1H), 8.29 (d, J=9.1 Hz, 1H), 8.06 (s, 1H), 7.62 (s, 1H), 7.43 (t, J=8.1 Hz, 1H), 7.28-7.23 (m, 2H), 6.63-6.59 (m, 1H), 4.06 (s, 3H), 2.75 (s, 3H). 13C NMR (125 MHz, CDCl3) δ 165.53, 152.95, 151.82, 148.42, 144.43, 143.32, 140.31, 134.59, 133.91, 129.93, 125.41, 120.77, 118.52, 113.87, 112.57, 112.24, 110.94, 52.73, 16.21.

Provenance & Evidence