Triethylamine → 4-(1-(4-methoxybenzyl)-3-vinyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine (3.68 g, 7.50 mmol, prepared according to the procedure for Example 7, Step B), potassium vinyltrifluoroborate (2.01 g, 15.0 mmol), triethylamine (2.08 ml, 15.0 mmol) and n-propanol (20 mL) was sparged with N2 for 5 min, and then Pd(dppf)Cl2 (0.306 g, 0.375 mmol) was added. The reaction was heated at 100° C. for 3 hours in a sealed vessel. After cooling to ambient temperature, the reaction was concentrated in vacuo. The residue was partitioned between DCM (30 mL) and water (30 mL). The phases were separated, and the aqueous phase was re-extracted with DCM (2×10 mL). The combined organic phases were dried (Na2SO4), filtered, and concentrated in vacuo. The crude was purified by Biotage Flash 65 chromatography system, eluting with 20% EtOAc/hexanes (1 L), 1:1 EtOAc/hexanes (1 L), then 2:1 EtOAc/hexanes (2 L). The product was obtained as a reddish colored solid (2.00 g, 64%).

Provenance & Evidence