反应详情

温度

150 °C

A mixture of 3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine (Intermediate F, 1.00 g, 5.3 mmol), 2-bromobenzamide (1.07 g, 5.3 mmol), potassium carbonate (0.89 g, 6.4 mmol), and copper (II) acetate (39 mg, 0.2 mmol) in DMF (20 mL) was heated (150° C.) in a sealed tube for 18 h. After cooling, the solution was adjusted to pH=4 using glacial acetic acid. The reaction mixture was extracted with dichloromethane (3×20 mL), and then the combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography of the residue over silica gel using 33-50% ethyl acetate/hexane afforded a yellow solid that was washed with diethyl ether to give 2-{[3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}benzamide (350 mg, 21%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 10.48 (s, 1H), 8.01 (s, 1H), 7.67 (dd, 1H), 7.32 (m, 7H), 6.77 (ddd, 1H), 6.08 (s, 1H), 2.19 (s, 3H), 2.00 (s, 3H); ES-MS m/z 307.1 (MH+); HPLC RT (min) 2.41.

1. temperatureAfter cooling
2. extractionThe reaction mixture was extracted with dichloromethane (3×20 mL)
3. washthe combined organic extracts were washed with brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customFlash chromatography of the residue over silica gel using 33-50% ethyl acetate/hexane afforded a yellow solid
8. washthat was washed with diethyl ether