Sodium Carbonate → HCID 66937077, compound

Participants

Reaction Conditions

Reaction Steps

5-fluoro-6-(3-fluorobenzylamino)pyridine-2-yl trifluoromethanesulfonate (0.0811 g, 0.220 mmol), 5-chloro-2-fluoropyridin-4-ylboronic acid (0.116 g, 0.661 mmol), and sodium carbonate (0.286 mL, 0.573 mmol, 2M in H2O) were dissolved in DME (2 mL). The solution was then degassed by sparging with argon for 5 min. It was then treated with PdCl2(dppf) CH2Cl2 adduct (0.036 g, 0.044 mmol). The reaction mixture was then heated in the microwave at 120° C. for 10 min. The reaction mixture was then filtered through a pad of Celite. The filtrate was concentrated in vacuo. The resulting residue was subjected to silica gel column chromatography. Elution using 5 EtOAc/95 hexanes to 60 EtOAc/40 hexanes yielded 0.044 g (57%) of 5′-chloro-2′,5-difluoro-N-(3-fluorobenzyl)-2,4′-bipyridin-6-amine. LCMS (m/z): 350.0 (MH+), retention time=1.16 min.

Provenance & Evidence