2-Amino-6-fluorobenzamide → 2-(4-bromo-1H-pyrazol-5-yl)-5-fluoroquinazolin-4(3H)-one

Participants

Reaction Steps

2-Amino-6-fluorobenzamide (77 mg, 0.50 mmol) was dissolved under argon in dimethylacetamide (5 ml), 4-bromo-1H-pyrazole-5-carbaldehyde (88 mg, 0.50 mmol) and Na2S2O5 (143 mg, 0.75 mmol) were added, and the mixture was stirred under reflux conditions for 5 h. After cooling to room temperature, the reaction mixture was concentrated and taken up with a mixture of acetonitrile and N,N-dimethylformamide. Filtration with suction and thorough drying of the remaining solid gave 2-(4-bromo-1H-pyrazol-5-yl)-5-fluoroquinazolin-4(3H)-one (30 mg, 19% of theory) as a colorless solid. 1H NMR (400 MHz, d6-DMSO δ, ppm) 13.91 (br. s, 1H, NH), 12.03 (br. s, 1H, NH), 8.22 (s, 1H), 7.80 (dd, 1H), 7.51 (d, 1H), 7.27 (dd, 1H).

Provenance & Evidence