Cesium carbonate → HCID 68758144, compound

Participants

Reaction Steps

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).

Provenance & Evidence