Potassium Carbonate → 3-[5-(4-Acetyl-3-hydroxy-2-methyl-phenoxymethyl)-[1,2,4]oxadiazol-3-ylmethyl]-benzoic acid

Participants

Reaction Steps

Combine 1-{2-hydroxy-4-[3-(3-iodo-benzyl)-[ 1,2,4]oxadiazol-5-ylmethoxy]-3-methyl-phenyl}-ethanone (150 mg, 0.32 mmol), sodium dodecyl sulfate (300 mg, 1.0 mmol), K2CO3 (45 mg, 0.32 mmol), 1-butanol (200 μL), and 1 drop of toluene in H2O (4 mL) in a pressure vessel, then degaswith Ar for 5 min. Add PdCl2(MeCN)2 (18 mg, 0.07 mmol) to the reaction mixture. Exchange the atmposphere with carbon monoxide and heat the mixture to 70° C. under 20 psi of carbon monoxide. The reaction is heated until complete. Filter the black mixture through filter cel. Acidify the filtrate with 5 N hydrochloric acid to pH=1. A milky white mixture forms. Add a small amount of methanol to induce crystallization Collect the crystals by filtration to give the title compound (79 mg, 65%). 1H NMR (DMSO-d6) δ 12.99 (s, 1H), 12.79 (s, 1H), 7.86 (m, 1H), 7.79 (m, 2H), 7.52 (m, 1H), 7.42 (dd, 1H), 6.67 (d, 1H), 5.60 (s, 2H), 4.19 (s, 2H), 2.55 (s, 3H), 1.99 (s, 3H). LC-MS (m/e): 381 (M−1).

Provenance & Evidence