2-Chloro-5-methyl-pyridine → 1-(4-(2-(4-(5-Methylpyridin-2-ylamino)phenoxy)pyridin-3-YL)piperidin-1-YL)ethanone

Participants

Reaction Conditions

Reaction Steps

Into a sealed tube were added 1-(4-(2-(4-aminophenoxy)pyridin-3-yl)piperidin-1-yl)ethanone (0.11 g, 0.37 mmol), 2-chloro-5-methylpyridine (0.043 g, 0.33 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.019 g, 0.02 mmol), 2-(dicyclohexylphosphino)-2′-methylbiphenyl (0.012 g, 0.034 mmol), sodium tert-butoxide (0.097 g, 1.01 mmol), and toluene (1.6 mL). After the mixture was degassed for 5 min, the reaction was stirred at 100° C. for 16 h. The cooled reaction was diluted with CH2Cl2 and washed with water. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. Flash column chromatography (20% to 80% EtOAc(10% MeOH)/Hexanes) gave a crude crop of the desired product. Further purification via reverse phase HPLC afforded 1-(4-(2-(4-(5-methylpyridin-2-ylamino)phenoxy)pyridin-3-yl)piperidin-1-yl)ethanone as a white amorphous solid. MS (ESI, pos. ion) m/z: 403.0 (M+1). IC50 (uM) 0.002844.

Provenance & Evidence