Thioglycolic Acid → 4-(4-Bromo-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 (1.74 g, 10 mmol), 4-bromo-2-methylbenzaldehyde (2.0 g, 10 mmol, Ark Pharm Inc.), and thioglycolic acid (3.90 g, 32 mmol) in acetonitrile (15 mL) was heated, in a sealed microwave vessel, for about 25 min, at about 150° C., in a microwave. After cooling to rt the precipitated solid was collected by filtration and washed with acetonitrile and diethyl ether to afford 4-(4-bromo-2-methyl-phenyl)-1-methyl-3-(2-pyridyl)-4,8-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one (2.92 g, 6.8 mmol, 68%), which was used as such. 1H-NMR (CDCl3, Bruker 400 MHz) δ 2.56 (3H, s), 3.29 (1H, d, J=15 Hz); 3.37 (1H, d, J=15 Hz); 3.95 (3H, s); 6.58 (1H, s); 6.66 (1H, d, J=8 Hz); 7.03 (2H, m); 7.24 (1H, d, J=11 Hz); 7.56 (1H, dt, J=8 Hz, 2 Hz); 7.75 (1H, m), 8.30 (1H, d, J=4 Hz).

Provenance & Evidence