Triethylamine → 5-Methylsulfanyl-3''-(propane-2-sulfonylamino)-[1,1';4',1'']terphenyl-2-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

Mix 4-Methylsulfanyl-2-trifluoromethanesulfonyloxy-benzoic acid methyl ester (1.216 g, 3.682 mmol), 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane (0.85 ml, 5.682 ), Et3N (1.55 ml, 11.121 mmol) and acetonitrile (40 ml) then heat to reflux for 16 hours. Dilute the reaction with EtOAc and wash with water. Concentrate under reduced pressure. Next add propane-2-sulfonic acid (4′-bromo-biphenyl-2-yl)-amide (0.532 g, 1.502 mmol) 2N Na2CO3 (7 ml, 14 mmol), 1,4-dioxane (35 ml) and tetrakis triphenyl phosphine palladium (0.177 g, 0.153 mmol). Heat to 80° C. for 16 hours. Cool the reaction, dilute with EtOAc, and wash with H2O, followed by saturated aqueous sodium chloride. Dry with Na2SO4 and concentrate under reduced pressure. Purify the reaction by flash chromatography (Silica gel-toluene then up to 20% EtOAc/Hexane) to give 5-Methylsulfanyl-3″-(propane-2-sulfonylamino)-[1,1′;4′,1″]terphenyl-2-carboxylic acid methyl ester (0.431 g, 63%). MS (m/e): 456(M+1).

Provenance & Evidence