Toluene → Tert-butyl 4-(3-(4-(5-chloropyridin-2-ylamino)phenoxy)pyrazin-2-yl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Into a sealed tube were added tert-butyl 4-(3-(4-aminophenoxy)pyrazin-2-yl)piperidine-1-carboxylate (0.31 g, 0.84 mmol), 2-bromo-5-chloropyridine (0.17 g, 0.92 mmol), palladium (II) acetate (0.019 g, 0.084 mmol), (rac)-BINAP (0.073 g, 0.12 mmol), cesium carbonate (0.49 g, 1.51 mmol), and toluene (4 mL). 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 aqueous layer was back-extracted with CH2Cl2 (1×). The organic extracts were combined, dried (MgSO4), filtered, and concentrated in vacuo. Flash column chromatography (10% to 40% EtOAc (10% MeOH)/Hexanes) provided tert-butyl 4-(3-(4-(5-chloropyridin-2-ylamino)phenoxy)-pyrazin-2-yl)piperidine-1-carboxylate as a yellow foam. MS (ESI, pos. ion) m/z: 482.1 (M+1).

Provenance & Evidence