N-Hydroxyphthalimide → 6-[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-propoxy]-4'-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester

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Reaction Steps

This compound was produced using similar methods as those used in Step 1, example 4, starting with 6-(3-bromo-propoxy)-4′-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester (0.60 g, 1.46 mmol), N-hydroxyphthalimide (0.30 g, 1.86 mmol) and N,N-diisopropylethylamine (0.36 g, 2.88 mmol). The crude material was purified by flash chromatography through silica gel using methylene chloride to give 6-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-propoxy]-4′-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester (0.50 g, 70%) as a white solid. 1H NMR (400 MHz, DMSO-d6); δ 8.01 (dd, 1H), 7.88 (d, 1H), 7.84 (s, 4H), 7.74 (s, 4H), 7.31 (d, 1H), 4.31 (t, 2H), 4.22 (t, 2H), 3.82 (s, 3H), 2.09 (m, 2H).

Provenance & Evidence