反应详情

温度

185 °C

To a 45 mL pressure bottle was added 2-fluoro-4-iodonicotinaldehyde (1.05 g, 4.18 mmol), 3-hydrazinylbenzenesulfonamide (800 mg, 4.27 mmol), and anhydrous NMP (15 mL). The reaction mixture was flushed with argon, securely capped, and heated at 185° C. for 6.5 h. The reaction mixture was cooled to room temperature and slowly added to a rapidly stirred solution of diethyl ether (430 mL). The resulting solid material was filtered and the pale yellow Et2O filtrate was allowed to stand for 18 h at room temperature. The yellow crystals precipitated out and were collected by vacuum filtration to give 425 mg (16.42%) of the title compound as a yellow solid as a “dot” 2 NMP complex by proton NMR. LC/MS (Condition B): ret. T=3.2 min, (M+H)+ 400.83. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.56 (s, 2 H) 7.78-7.84 (m, 2 H) 7.89-7.92 (m, 1 H) 8.37-8.42 (m, 2 H) 8.57 (dt, J=4.81, 2.33 Hz, 1 H) 8.75 (s, 1 H). Second and third crops of yellow solid (300 mg, 11.7%; 246 mg, 9.4%) were identical to the first crop of material.

1. customThe reaction mixture was flushed with argon
2. customsecurely capped
3. temperatureThe reaction mixture was cooled to room temperature
4. additionslowly added to a rapidly stirred solution of diethyl ether (430 mL)
5. filtrationThe resulting solid material was filtered
6. customThe yellow crystals precipitated out
7. filtrationwere collected by vacuum filtration