Cesium carbonate → (E)-ethyl 3-(5-(benzylthio)-2-((5,6-dichloro-2-methoxypyridin-3-yl)amino)phenyl)acrylate

Participants

Reaction Conditions

Reaction Steps

A RBF was charged with (E)-ethyl 3-(2-amino-5-(benzylthio)phenyl)acrylate (2.0 g, 6.38 mmol)), 2,3-dichloro-5-iodo-6-methoxypyridine (2.327 g, 7.66 mmol)), xantphos (0.185 g, 0.319 mmol)), Pd2(dba)3 (0.146 g, 0.160 mmol)), and cesium carbonate (2.91 g, 8.93 mmol)) were added. A reflux condenser was attached and the flask was heated at 90° C. overnight. The mixture was cooled to RT, diluted with EtOAc, and filtered through celite, with the aid of EtOAc. The filtrate was concentrated and i-PrOH was added. The mixture was heated to 110° C. until all the material dissolved, then the solution was allowed to cool to RT overnight causing a yellow solid to crash out of solution. The solids were filtered and washed with i-PrOH, then dried under a nitrogen blanket to afford (E)-ethyl 3-(5-(benzylthio)-2-((5,6-dichloro-2-methoxypyridin-3-yl)amino)phenyl)acrylate (2.54 g, 5.19 mmol, 81% yield) as a yellow solid. m/z (ESI) 491.1 (M+H)+.

Provenance & Evidence