Ethyl Acetate → Trifluoro-methanesulfonic acid 3-(3,5-Dichloro-4'-carboxymethyl-biphenyl-4-ylmethyl)-1-(4,5,6,7-tetrahydro-2H-indazol-5-yl)-pyrrolidin-2-one

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Reaction Steps

Combine Trifluoro-methanesulfonic acid 3,5-dichloro-4-[2-oxo-1-(2-trifluoromethanesulfonyl-4,5,6,7-tetrahydro-2H-indazol-5-yl)-pyrrolidin-3-ylmethyl]-phenyl ester (1.0 g, 1.55 mmol), 4-Carboxymethylphenyl boronic acid (0.416 g, 2.3 mmol), sodium carbonate (2.3 ml of 2.0 M, 5.4 mmol) in DME (12 mL) and degas with a stream of nitrogen. Add (Ph3P)4Pd (0.078 g, 0.15 mmol), and stir at 80° C. for 17 hour under nitrogen atmosphere. Cool to ambient temperature and add ethyl acetate (20 mL) and water (10 mL). Extract the aqueous phase with ethyl acetate (2×20 mL), dry (sodium sulfate) and condense under reduced pressure. Chromatography (silica, 95:5 CH2Cl2/Methanol) yields 0.750 g as a white solid MS (m/z): 632 (M+2).

Provenance & Evidence