反应详情

温度

0 °C

Bromine (1.39 mL, 27.03 mmol) was added drop wise over 5 minutes to a solution of 1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol (6.00 g, 23.50 mmol, prepared as described in WO 2007/103308) in absolute ethanol (60 mL) at 0° C. The reaction was stirred at 0° C. for 1 hour. 5% Sodium bicarbonate solution (100 mL) was then added, and the mixture was concentrated to give a slurry. The pH was next adjusted with 1N HCl to a pH of 4. The resulting solid was collected by filtration and dried. This solid was then suspended in ether (50 mL), stirred for 10 minutes, collected by filtration and dried to give 5-bromo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol (6.8 g, 87%). MS ESI (+) m/z 334 detected. 1H NMR (400 Hz, DMSO-d6) δ 12.68 (s, 1H), 8.34 (s, 1H), 8.13 (s, 1H), 7.18 (d, J=8.8 Hz, 2H), 6.87 (d, J=8.4 Hz, 2H), 5.47 (s, 2H), 3.70 (s, 3H).

1. concentrationthe mixture was concentrated
2. customto give a slurry
3. filtrationThe resulting solid was collected by filtration
4. customdried
5. stirringstirred for 10 minutes
6. filtrationcollected by filtration
7. customdried