5-(1-Phenylethyl)benzofuran-2-ylboronic acid → Methyl 1-((3-fluoro-4-(5-(1-phenylethyl)benzofuran-2-yl)phenyl)methyl)azetidine-3-carboxylate

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Reaction Steps

According to Scheme B2 and general procedure F, methyl 1-(4-bromo-3-fluorobenzyl)azetidine-3-carboxylate (0.241 g, 0.797 mmol) and 5-(1-phenylethyl)benzofuran-2-ylboronic acid (0.212 g, 0.797 mmol) were employed to give methyl 1-((3-fluoro-4-(5-(1-phenylethyl)benzofuran-2-yl)phenyl)methyl)azetidine-3-carboxylate. According to Scheme B2 and general procedure H, methyl 1-((3-fluoro-4-(5-(1-phenylethyl)benzofuran-2-yl)phenyl)-methyl)azetidine-3-carboxylate (0.275 g, 0.620 mmol) provided 1-((3-fluoro-4-(5-(1-phenylethyl)benzofuran-2-yl)phenyl)methyl)azetidine-3-carboxylic acid as a white solid [hS1P1 EC50=99 nM]. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.89 (t, J=8.0 Hz, 1H), 7.59 (s, 1H), 7.53 (d, J=8.5 Hz, 1H), 7.20-7.35 (m, 8H), 7.12-7.20 (m, 1H), 4.28 (q, J=7.0 Hz, 1H), 3.60 (s, 2H), 3.18-3.46 (m, 5H), 1.64 (d, J=7.5 Hz, 3H). MS (ESI) m/z: Calculated: 429.2; Observed: 430.2 (M++1).

Provenance & Evidence