Morpholine → HCID 59374222, compound

Participants

Reaction Conditions

Reaction Steps

A microwave reaction vessel was charged with tert-butyl 4-(3-bromopyridin-2-yloxy)phenyl(pyridin-2-yl)carbamate (0.6142 g, 1.39 mmol), palladium (II) acetate (0.0306 g, 0.0833 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (0.0932 g, 0.167 mmol), and sodium tert-butoxide (0.5219 g, 4.17 mmol). The vessel was put under vacuum for 5 min. A solution of morpholine (0.316 mL, 2.78 mmol) in toluene was added to the vessel. The reaction was allowed to heat at 90° C. for 10 min. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage™ pre-packed silica gel column (40M), eluting with a gradient of 10% to 50% acetone in hexane. Product was taken up in DCM and TFA was added to stir overnight. The solvent was removed and the residue was filtered through a carbonate filter to provide N-(4-(3-morpholinopyridin-2-yloxy)phenyl)pyridin-2-amine. MS (ESI, pos. ion) m/z: 349.1 (M+1). IC50 (uM) 0.030207.

Provenance & Evidence