Sodium Carbonate → HCID 46216224, compound

Participants

Reaction Steps

To a round bottomed flask was added (4-(3-bromopyridin-2-yloxy)phenyl)(1H-imidazo[4,5-b]pyridin-2-yl)methanone (0.250 g, 0.633 mmol), pyridin-3-ylboronic acid (0.233 g, 1.898 mmol), PdCl2(dppf) (0.035 g, 0.063 mmol), and sodium carbonate (0.335 g, 3.16 mmol) in DMSO (1.581 mL) and Water (0.527 mL) at 80° C. to stir overnight. The reaction was worked up via seperatory funnel. The crude product was purified by reverse-phase preparative HPLC using a Phenomenex Synergi column, 4 micron, MAX-RP, 80 Å, 150×30 mM, 0.1% TFA in ACN/H2O, gradient 25% to 100% over 15 min to provide (4-(3,3′-bipyridin-2-yloxy)phenyl)(1H-imidazo[4,5-b]pyridin-2-yl)methanone. MS (ESI, pos. ion) m/z: 394.0 (M+1). IC50 (uM) +++++.

Provenance & Evidence