Cesium carbonate → 6-(benzylthio)-1-(2-chloro-3'-fluoro-5-methoxy-[1,1'-biphenyl]-4-yl)-1,8-naphthyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

A vial was charged with 2-chloro-3′-fluoro-5-methoxy-[1,1′-biphenyl]-4-amine (302 mg, 1.198 mmol), (E)-ethyl 3-(5-(benzylthio)-2-chloropyridin-3-yl)acrylate (400 mg, 1.198 mmol), Xantphos (69.3 mg, 0.120 mmol), Pd2 dba3 (54.9 mg, 0.060 mmol), cesium carbonate (781 mg, 2.396 mmol) and 1,4-dioxane (4793 pp. The mixture was purged with argon, the vial was sealed, and the reaction was heated at 100° C. for 5 h. Upon cooling to RT, 10 mL methanol was added, and the mixture was heated at 80° C. for 2 h. Upon cooling to RT the mixture was loaded onto silica gel and purified using 0-50% EtOAc/heptane to provide 6-(benzylthio)-1-(2-chloro-3′-fluoro-5-methoxy-[1,1′-biphenyl]-4-yl)-1,8-naphthyridin-2(1H)-one (410 mg, 0.815 mmol, 68.0% yield) as a light orange foamy solid. m/z (ESI) 503.0 (M+H)+.

Provenance & Evidence