Phenyl dihydrogen orthoborate → HCID 11166539, compound

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Reaction Steps

To a solution of 3-{[2-(4-chloro-3-trifluoromethyl-phenyl)-benzofuran-5-ylmethyl]-amino}-propionic acid tert-butyl ester (1 eq) and phenyl boric acid (1.5 eq) in THF (0.5 M) is added palladium(II) acetate (0.1 eq), 2-(dicyclohexylphosphino)biphenyl (0.2 eq) and potassium fluoride (4.0 eq). The mixture is irradiated with microwave at 120° C. for 45 minutes. The product, 3-{[2-(2-trifluoromethyl-biphenyl-4-yl)-benzofuran-5-ylmethyl]-amino}-propionic acid tert-butyl ester, is purified with column chromatography. The ester is hydrolyzed with TFA in CH2Cl2 (1:2, v/v) at room temperature. It is purified with preparative LCMS to afford 3-{[2-(2-trifluoromethyl-biphenyl-4-yl)-benzofuran-5-ylmethyl]-amino}-propionic acid, which is converted to HCl salt: 1H NMR (400 MHz, CD3OD) δ 8.29 (d, 1H), 8.18 (dd, 1H), 7.82 (d, 1H), 7.71 (d, 1H), 7.55-7.30 (m, 8H), 4.36 (s, 2H), 3.32 (t, 2H), 2.77 (t, 2H); MS (ES) 440.2 (M+H+).

Provenance & Evidence