Triethylamine → N-(4-((4-methoxyphenyl)sulfonyl)phenyl)acetamide

Participants

Reaction Conditions

Reaction Steps

To a solution of sodium 4-acetamidobenzenesulfinate dehydrate (128 mg, 0.5 mmol), 4-methoxy-phenylboronic acid (114 mg, 0.75 mmol) and Et3N (0.313 mL, 2.25 mmol) in 1,4-dioxane (4 mL) and DMSO (4 mL) is added Cu(OAc)2 (114 mg, 0.625 mmol). The mixture is heated at 60° C. for 16 h then cooled to ambient temperature. EtOAc (12 ml) and brine (6 ml) is added followed by concentrated NH4OH (0.6 mL) and the mixture is stirred at ambient temperature for 15 min. The layers are separated and the aqueous layer is extracted with EtOAc (6 mL). The combined extracts are dried (Na2SO4) and evaporated. The residue is purified by preparative TLC with 2:1 EtOAc/hexanes to give 111 mg (72%) white solid.

Provenance & Evidence