Lithium Chloride → 5-(3-fluoro-4-(1-(4-methoxybenzyl)-3-(4-(morpholine-4-carbonyl)phenyl)-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 (0.013 g, 0.019 mmol), 4-(morpholine-4-carbonyl)phenylboronic acid (0.005 g, 0.02 mmol), Pd(PPh3)4 (0.001 g, 0.0009 mmol) and lithium chloride (0.003 g, 0.08 mmol) in dioxane (0.5 mL) and 2 M aqueous Na2CO3 (0.5 mL) was stirred at 100° C. for 1 hour. The reaction mixture was cooled to room temperature and then 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 0.014 g crude product as a yellow gum. The crude material was used without further purification in the following step. LRMS (APCI pos) m/e 738 (M+1).

Provenance & Evidence