Cesium carbonate → 4-(2-(4-(Benzo[d]thiazol-2-ylamino)phenoxy)pyridin-3-yl)-1-methylpiperidin-2-one

Participants

Reaction Conditions

Reaction Steps

Into a sealed tube were added 4-(2-fluoropyridin-3-yl)-1-methylpiperidin-2-one (0.06 g, 0.288 mmol), 4-(benzo[d]thiazol-2-ylamino)phenol (0.223 g, 0.922 mmol), cesium carbonate (0.310 g, 0.951 mmol), and 1-methyl-2-pyrrolidinone (1 mL). After degassing for 5 min, the reaction was heated at 120° C. for 14 h. The cooled mixture was diluted with EtOAc and washed with water; the aqueous layer was back-washed with EtOAc (1×). The combined organic extracts were washed with aqueous 1N NaOH solution, dried (MgSO4), filtered, and concentrated in vacuo. Flash column chromatography (20% to 100% EtOAc/Hexanes) afforded 4-(2-(4-(benzo[d]thiazol-2-ylamino)phenoxy)pyridin-3-yl)-1-methylpiperidin-2-one (0.046 g, 37.1% yield) as a tan amorphous solid. MS (ESI, pos. ion) m/z: 431.9 (M+1). IC50 (uM) +++++.

Provenance & Evidence