m-Toluidine → HCID 67221076, compound

Participants

Reaction Conditions

Reaction Steps

[3-(2-{[(4-Bromo-benzenesulfonyl)-ethyl-amino]-methyl}-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid methyl ester (0.183 g, 0.31 mmol), m-toluidine (0.04 mL, 0.38 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.009 g, 0.02 mmol) were combined in 1,4-dioxane (3.6 mL). Cesium carbonate (0.505 g, 1.55 mmol) and tris(dibenzylideneacetone)dipalladium (0) (0.028 g, 0.03 mmol) were added, and the mixture was purged with N2 for 15 minutes and then stirred at 70° C. overnight under N2. Once no starting material was seen by analytical LCMS, the mixture was filtered through Celite. The filter cake was washed with EtOAc, and the filtrate was concentrated and purified by silica gel chromatography (10-30% EtOAc in hexanes) to give the title compound.

Provenance & Evidence