Sodium Carbonate → N-[(6-chloro-3'-formyl-3-biphenylyl)methyl]-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}propanediamide

Participants

Reaction Steps

A mixture of N-[(3-bromo-4-chlorophenyl)methyl]-N′-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}propanediamide (1.06 g, 1.791 mmol), (3-formylphenyl)boronic acid (0.330 g, 2.2 mmol), tetrakis (triphenylphosphine) palladium (0) (0.092 g, 0.08 mmol), sodium carbonate (0.212 g, 2.0 mmol) in 1,4-dioxane (12 mL) and water (4 mL) was microwaved at 140° C. for 30 min. The reaction mixture was diluted with water and EtOAc; layers were separated. The aqueous phase was re-extracted with EtOAc. The combined organic extracts were dried over Na2SO4 and evaporated to a residue. This residue was purified on the Chromatotron on silica gel (2000u) eluting with CH2Cl2 (3-6% MeOH) to give N-[(6-chloro-3′-formyl-3-biphenylyl)methyl]-N′-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}propanediamide (752.4 mg, 68.1%) as a glassy solid. LC-MS m/z 617.3 (M+H)+, 0.86 min (ret time).

Provenance & Evidence