p-Bromophenoxyacetic acid → {4'-[3-(Propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-4-yloxy}-acetic acid

Participants

Reaction Steps

Heat a solution of (4-Iodo-phenoxy)-acetic acid or (4-bromo-phenoxy)-acetic acid (0.25 mmol), propane-2-sulfonic acid {2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-thiophen-3-yl}-amide (122 mg, 0.30 mmol), PdCl2(dppf)(41 mg, 0.05 mmol) and barium hydroxide (158 mg, 0.50 mmol) in DMF-H2O (v/v 4:1, 2.5 mL) to 80° C. under nitrogen atmosphere for 20 h. Pour into H2O (50 mL) and dichloromethane (50 mL), then extract with H2O (4×50 mL) and dry the combined organic phases (MgSO4). Concentrate to furnish a crude mixture as a yellowish solid. Purification by flash chromatography (Silica gel-Hexane/EtOAc) affords the title compound as a pale yellow solid (65-80% yield). MS (ES−):430.1 (M−1).

Provenance & Evidence