Carbonic Acid → N-(4-(3,3'-Bipyridin-2-yloxy)phenyl)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(4-(3-Bromopyridin-2-yloxy)phenyl)pyridin-2-amine hydrochloride (0.257 g, 0.68 mmol), 3-pyridineboronic acid (0.115 g, 0.94 mmol), sodium carbonate anhydrous (0.358 g, 3.4 mmol) and trans-dichlorobis(triphenylphosphine)palladium (II) (0.045 g, 0.064 mmol) in 6:3:2 DME:H2O:EtOH was sealed under argon in a microwave tube and heated at 145° C. for 15 min in the microwave (Emrys by Personal Chemistry). The reaction was filtered and the filtrate was partitioned between EtOAc/brine. The aqueous layer was extracted with EtOAc (3×) and the combined organic layers were evaporated onto silica gel and purified by flash chromatography [Isco, (40 gram)] eluting with 2M NH3 in MeOH:CH2Cl2 (0:1→3:97) to give a white amorphous solid. MS (ESI, pos. ion) m/z: 341.1 [M+1]. IC50 (uM) 0.002612.

Provenance & Evidence