Sodium Carbonate → HCID 178518666, compound

Participants

Reaction Conditions

Reaction Steps

Boronic acid solution 0.1 M was prepared in Toluene/EtOH (1/1). Boronic acid solution (100 mmol, 1000 μL) was added to vials. A suspension of 5-(3-bromophenyl)-7-((4-methoxyphenyl)amino)-5H-pyrazolo[3′,4′:4,5]pyrido[2,3-d]pyrimidin-3-ol (16) 0.1 M was prepared in Toluene/EtOH (1/1). Suspension of intermediate 56 (500 μL, 50 mmol) was added into each vial. Saturated Na2CO3 (500 μL) was added to each vial. Add catalytic amount of BDtBFPdCl2 to each vial at a time followed by purging with N2 with pipette and cap the vial immediately. The reactions were shaken at 100° C. for at least 16 h. EtOAc (2 mL) was added to each vial. Water (0.5 mL) was added to each vial. Vortex vials and water layer was removed. Additional water (1500 μL) was added to each vial, vortex and remove the water layer. Repeat water washing sequence again. Solvents were removed to dryness. Residue was dissolved in DMSO (1 mL) (may need heat to dissolve or add one drop TFA) and purified by reverse phase HPLC. To obtain 5-(4′-fluoro-[1,1′-biphenyl]-3-yl)-7-(4-methoxyphenyl)amino)-2H-pyrazolo[3′,4′:4,5]pyrido[2,3-d]pyrimidin-4(5H)-one (Compound 133) (11.2 mmol, 22%) LC-Mass: m/e 479 (M+1).

Provenance & Evidence