Toluene → 1-(4-(3-(4-(5-Methylpyridin-2-ylamino)phenoxy)pyrazin-2-yl)piperidin-1-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

Into a sealed tube were added 2-chloro-5-methylpyridine (0.055 g, 0.431 mmol), 1-(4-(3-(4-aminophenoxy)pyrazin-2-yl)piperidin-1-yl)ethanone (0.148 g, 0.474 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.024 g, 0.026 mmol), 2-(dicyclohexylphosphino)-2′-methylbiphenyl (0.016 g, 0.043 mmol), sodium tert-butoxide (0.124 g, 1.293 mmol), and toluene (2.16 mL, 0.431 mmol). After the mixture was degassed for 5 min, the reaction was stirred at 100° C. for 18 h. The cooled reaction was diluted with CH2Cl2 and washed with water. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. ISCO purification (20% to 80% EtOAc (10% MeOH)/Hexanes), followed by reverse phase HPLC (Shimadzu) afforded 1-(4-(3-(4-(5-methylpyridin-2-ylamino)phenoxy)pyrazin-2-yl)piperidin-1-yl)ethanone as a white amorphous solid. MS (ESI, pos. ion) m/z: 404.0 (M+1). IC50 (uM) 0.00004.

Provenance & Evidence