反应详情

A solution of tert-butyl 4-(5-bromo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.30 g, 0.597 mmol, see Example 1), 3-fluorophenylboronic acid (0.125 g, 0.896 mmol), Pd(PPh3)4 (0.0690 g, 0.0597 mmol) and Cs2CO3 (0.778 g, 2.39 mmol) in dioxane:H2O (8 mL, 3:1) was heated at 80° C. for 6 hours. Ether (50 mL) and H2O (20 mL) were then added. The organic layer was separated, washed with brine and dried over sodium sulfate. After removal of solvent, the resulting residue was purified by column chromatography (DCM:ethyl acetate, 5:1) to give tert-butyl 4-(5-(3-fluorophenyl)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.25 g, 81%) as a solid. MS ESI (+) m/z 518.4 detected. 1H NMR (400 Hz, DMSO-d6) δ 8.31 (s, 1H), 8.16 (s, 1H), 7.51 (m, 1H), 7.39 (m, 2H), 7.23 (d, J=8.8 Hz, 2H), 7.18 (m,l H), 6.86 (d, J=8.8 Hz, 2H), 5.53 (s, 2H), 3.70 (s, 3H), 3.29 (m, 4H), 3.25 (m, 4H).

1. customThe organic layer was separated
2. washwashed with brine
3. dry with materialdried over sodium sulfate
4. customAfter removal of solvent
5. customthe resulting residue was purified by column chromatography (DCM:ethyl acetate, 5:1)