Sodium hydride → tert-butyl 4-(5-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

関与物質

反応条件

反応手順

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).

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