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}butanediamide

Participants

Reaction Steps

A solution 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}butanediamide (1.0 g, 1.650 mmol), (3-formylphenyl)boronic acid (0.300 g, 2.00 mmol), tetrakis (triphenylphosphine) palladium (0) (0.092 g, 0.08 mmol) and sodium carbonate (0.509 g, 4.8 mmol) in 1,4-dioxane (12 mL) and water (4.00 mL) was microwaved at 140° C. for 30 min. The reaction was diluted with water and EtOAc and the organic layer taken off. The aqueous phase was re-extracted with EtOAc. The combined organic layers were dried over Na2SO4 and solvent was evaporated giving a residue. The crude material 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}butanediamide (861 mg, 83%) as a glassy solid. LC-MS m/z 631.4 (M+H)+, 0.86 min (ret time).

Provenance & Evidence