Hydrochloric Acid → HCID 69298434, compound

Participants

Reaction Steps

To a mixture of 3-(2-methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridine (0.3 g, 0.62 n mmol) and 1-(3-bromo-phenyl)-butane-1(S),2(S)-diol (0.152 g, 0.62 mmol) in a 20 mL microwave reaction flask was added THF (3 mL), acetonitrile (3 mL), and sodium carbonate (1 N in water, 3 mL, 6 n mmol). The resulting suspension was purged with nitrogen for 1 minute. Dichloro[1,1′-bis(diphenylphoshino)ferrocene]palladium(II) dichloromethane adduct (22 mg, 27 μmol) was added and the purging was continued for another minute. The flask was sealed and irradiated in a microwave reactor to 90° C. for 10 minutes. The reaction mixture was neutralized to pH 7 using 1 N hydrochloric acid, extracted with ethyl acetate (10 mL×3). The combine organic layers were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexane to afford 1-{3-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-butane-1,2-diol as a off white solid (171 mg, 53%). MS: m/z 520 (M+H+).

Provenance & Evidence