4-Fluorophenylboronic acid → 5-(3-fluoro-4-(3-(4-fluorophenyl)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-(3-fluoro-4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one (0.025 g, 0.0371 mmol; prepared according to the procedure of Example 86, Step E), 4-fluorophenylboronic acid (0.006 g, 0.04 mmol), Pd(PPh3)4 (0.002 g, 0.002 mmol) and lithium chloride (0.006 g, 0.15 mmol) in dioxane (1 mL) and 2 M aqueous Na2CO3 (1 mL) was stirred at 110° C. for 35 minutes and then at ambient temperature overnight. The reaction mixture was partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was re-extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated to yield 0.031 g crude product as a yellow gum. The crude material was used without further purification in the following step. LRMS (APCI pos) m/e 643 (M+1).

Provenance & Evidence