Thioglycolic Acid → 4-(4-Bromo-2-chloro-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 (1.6 g, 9.2 mmol), 4-bromo-2-chloro-benzaldehyde (2.0 g, 9.1 mmol, Apollo Scientific), and thioglycolic acid (3.4 g, 37 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 (4 mL) to afford 4-(4-bromo-2-chloro-phenyl)-1-methyl-3-(2-pyridyl)-4,8-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one (2.86 g, 6.4 mmol, 70%), which was used as such. 1H-NMR (CDCl3, Bruker 400 MHz) δ 3.10 (1H, d, J=12 Hz); 3.43 (1H, d, J=12 Hz); 3.86 (3H, s); 6.68 (1H, s); 6.93 (1H, d, J=8 Hz); 7.15 (1H, m); 7.28 (1H, dd, J=2 Hz, 8 Hz); 7.65 (1H, d, J=2 Hz); 7.70 (1H, dd, J=2 Hz, 8 Hz), 7.78 (1H, d, J=8 Hz); 8.34 (1H, d, J=4 Hz); 10.2 (1H, s).

Provenance & Evidence