(Naphthalen-2-yl)boronic acid → 4-(2-Naphthyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazole

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Reaction Conditions

Reaction Steps

To a solution of E1 (1.0 eq.) in benzene (0.1 M solution), 2-naphthylboronic acid (1.5 eq.) and sat. aq. Na2CO3 solution under argon was added PdCl2((PPh)3)2. The mixture was stirred for 72 hr at 60° C., then cooled and then extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure. The crude was purified by column chromatography on silica gel eluting with 20-50% EtOAc/petroleum ether to obtain E2 as yellow solid. 1H NMR (300 MHz, CDCl3) δ: 8.31 (1H, s), 7.88-7.70 (5H, m), 7.48-7.39 (3H, m), 5.28 (2H, s), 3.54 (2H, t, J=8.2 Hz), 0.94 (2H, t, J=8.2 Hz), 0.00 (9H, s). MS (ES) C19H24N2OSi requires: 324, found: 325 (M+H)+.

Provenance & Evidence