Thioglycolic Acid → 4-(4-Chloro-2-methyl-phenyl)-1-methyl-3-(2-pyridyl)-4,8-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-methyl-3-(2-pyridyl)pyrazol-5-amine (1.1 g, 6.3 mmol), 4-chloro-2-methylbenzaldehyde (1.0 g, 6.5 mmol, Fluorochem), and thioglycolic acid (2.4 g, 26 mmol) in acetonitrile (20 mL) was heated, in a sealed microwave vessel, for about 20 min, at about 150° C., in a microwave. After cooling to rt the precipitated solid was collected by filtration and washed with acetonitrile (2 mL) to afford 4-(4-chloro-2-methyl-phenyl)-1-methyl-3-(2-pyridyl)-4,8-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one (1.16 g, 3.0 mmol, 48%), which was used as such. 1H-NMR (CDCl3, Bruker 400 MHz) δ 2.50 (3H, s); 3.07 (1H, d, J=12 Hz); 3.50 (1H, d, J=12 Hz); 3.84 (3H, s); 6.59 (1H, s); 6.86 (1H, d, J=8 Hz); 6.98 (1H, m); 7.1-7.2 (2H, m); 7.68 (1H, m), 7.76 (1H, d, J=6 Hz), 8.4 (1H, s), 10.2 (1H, s).

Provenance & Evidence