Cesium carbonate → HCID 117746874, compound

Participants

Reaction Steps

A RBF was charged with (E)-ethyl 3-(2-amino-5-(benzylthio)phenyl)acrylate (8.25 g, 26.3 mmol, made via Method 42, Steps 1-2), 2-bromo-4-chloro-1-iodobenzene (10.02 g, 31.6 mmol), Xantphos (0.762 g, 1.316 mmol), Pd2(dba)3 (0.603 g, 0.658 mmol), and cesium carbonate (21.44 g, 65.8 mmol) were added. A reflux condenser was attached and the flask was lowered into a 110° C. heating bath for 1 h. The mixture was cooled to room temperature then filtered through celite with the aid of toluene. The filtrate was concentrated. The residue was taken up in 2-PrOH and concentrated to give a yellow solid with some tan chunks. The mixture was taken up in 2-PrOH and the resulting slurry was heated to boiling for 5 min to give a brown solution (after breaking up some solid with a spatula). The resulting solution was allowed to cool to RT while being stirred. The mixture became a thick slurry that was diluted with 2-PrOH and filtered. The collected solid was washed with 2-PrOH (3×), then dried under a stream of N2 (g) to give (E)-ethyl 3-(5-(benzylthio)-2-((2-bromo-4-chlorophenyl)amino)phenyl)acrylate (10.473 g, 20.83 mmol, 79% yield) as a bright-yellow solid. 1 H NMR (400 MHz, DMSO-d6)□=7.76-7.61 (m, 4 H), 7.38-7.27 (m, 5 H), 7.27-7.20 (m, 2 H), 6.88 (d, J=8.4 Hz, 1 H), 6.62-6.52 (m, 2 H), 4.27 (s, 2 H), 4.14 (q, J=7.1 Hz, 2 H), 1.22 (t, J=7.1 Hz, 3 H). m/z (ESI) 502.0 (M+H)+.

Provenance & Evidence