Sodium Carbonate → HCID 66589203, compound

Participants

Reaction Steps

3-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)propanenitrile (1.75 mmol) was dissolved in toluene (32 mL) and ethanol (19 mL). 4-Aminophenylboronic acid, pinacol ester (858 mg, 3.9 mmol) was added followed by the addition of a 2M aqueous solution of Na2CO3 (7.1 mL). The mixture was degassed by bubbling a stream of nitrogen through the solution and tetrakis(triphenylphosphine)palladium (53 mg) was added. The mixture was heated under reflux for 4 h, cooled to room temperature and concentrated. The mixture was dissolved in ethyl acetate and washed with brine. The organic phase was dried over MgSO4, filtered and concentrated. The crude product was applied to a silica gel column and eluted with ethyl acetate in hexanes (30-100%) to give 547 mg of the title compound.

Provenance & Evidence