反应详情

温度

40 °C

Sodium hydride (0.0881 g, 2.20 mmol) in DMF (5 mL) was added dropwise to 5-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol (0.70 g, 1.84 mmol) in DMF (5 mL). Then the reaction mixture was warmed to 40° C. and stirred for 30 minutes. After cooling to room temperature, 1,1,1-trifluoro-N-phenyl-N-(trifluoromethylsulfonyl)methanesulfonamide (0.787 g, 2.20 mmol) was added and stirred at room temperature for 1 hour. tert-Butyl piperazine-1-carboxylate (0.787 g, 4.22 mmol) was then added, and the mixture was stirred at 80° C. for 1 hour. Saturated NH4Cl (20 mL) was added, and the reaction was extracted with ethyl acetate and dried over sodium sulfate. After removal of the solvent, the resulting residue was purified by column chromatography (hexane:ethyl acetate, 5:1) to give tert-butyl 4-(5-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.94 g, 93%) as a solid. MS ESI (+) m/z 550.3 detected. 1H NMR (400 Hz, DMSO-d6) δ 8.64 (s, 1H), 8.31 (s, 1H), 7.20 (d, J=7.6 Hz, 2H), 6.82 (d, J=7.6 Hz, 2H), 5.52 (s, 2H), 3.69 (s, 3H), 3.56 (m, 4H), 3.46 (m, 4H), 1.44 (s, 9H).

1. temperatureAfter cooling to room temperature
2. stirringstirred at room temperature for 1 hour
3. stirringthe mixture was stirred at 80° C. for 1 hour
4. extractionthe reaction was extracted with ethyl acetate
5. dry with materialdried over sodium sulfate
6. customAfter removal of the solvent
7. customthe resulting residue was purified by column chromatography (hexane:ethyl acetate, 5:1)