2-Chloropyridine → N-(4-(3-(pyridin-4-yl)pyridin-2-yloxy)phenyl)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 4-(3-(pyridin-4-yl)pyridin-2-yloxy)benzenamine (0.0965 g, 0.37 mmol), 2-chloropyridine (0.034 mL, 0.36 mmol), palladium(II) acetate (0.0098 g, 0.018 mmol), BINAP (0.0213 g, 0.037 mmol), and sodium tert-butoxide (0.0503 g, 0.55 mmol). The reaction mixture was stirred and heated in a Smith Synthesizer® microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 120° C. for 45 min. Reaction was concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage™ pre-packed silica gel column (25M), eluting with a gradient of 1% to 5% methanol in DCM, to provide N-(4-(3-(pyridin-4-yl)pyridin-2-yloxy)phenyl)pyridin-2-amine. MS (ESI, pos. ion) m/z: 341.1 (M+1). IC50 (uM) 0.000659.

Provenance & Evidence