Sodium Hydroxide → tert-Butyl (1-{4-[2-(2-aminopyridin-3-yl)-5-{3-[(2-hydroxyethyl)amino]phenyl}-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutyl)carbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl (1-{4-[2-(2-aminopyridin-3-yl)-5-chloro-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}cyclobutyl)carbamate (70.0 mg, 0.143 mmol), 2-{[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amino}ethanol (75.0 mg, 0.285 mmol), bis(di-tert-butyl(4-dimethylaminophenyl) phosphine)dichloropalladium(II) (10.1 mg, 0.0143 mmol), and 2M NaOH aq. (0.430 mL, 0.214) in DMF (2 mL) was heated at 160° C. for 1 hour under microwave irradiation. After cooling to room temperature, the mixture was diluted with EtOAc and washed with water (3×) and brine. The combined organic layers were dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica gel column chromatography (CHCl3/EtOAc=1:1→1:2→EtOAc) to afford desired product (73.0 mg, 86.5%) as yellow solid.

Provenance & Evidence