Sodium Carbonate → N-(3-fluoro-4-(1-(4-methoxybenzyl)-3-(4-(methylcarbamoyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

A 50 mL round-bottomed flask was charged with N-(4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-1-methyl-2-oxopyrrolidine-3-carboxamide (20.0 mg, 0.0325 mmol), 4-(methylcarbamoyl)phenylboronic acid (17.5 mg, 0.0975 mmol), tetrakis(triphenylphosphine) palladium (7.51 mg, 0.00650 mmol), Na2CO3 (0.0812 ml, 0.162 mmol) and DME (10 mL). The reaction mixture was stirred at 60° C. for 4 hours, and then partitioned between EtOAc and H2O. The phases were separated, and the aqueous phase was re-extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated to yield a crude product. The crude product was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 100/1 to 10/1, v/v) to afford product (10.8 mg, 53.4%). LRMS (APCI pos) m/e 623 (M+1).

Provenance & Evidence