2-Ethylphenylboronic Acid (contains varying amounts of Anhydride) → Quinuclidin-3-yl2'-ethylbiphenyl-3-ylcarbamate

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Reaction Steps

Using general procedure E, quinuclidin-3-yl3-bromophenylcarbamate, 2-ethylphenylboronic acid and [PdCl2(pddf)]CH2Cl2 gave the title vcompound as a white solid (110 mg, 78%). 1H NMR (400 MHz, CDCl3) δ 7.42-7.28 (m, 5H), 7.25-7.16 (m, 2H), 7.03-7.00 (m, 1H), 6.88 (br s, 1H), 4.83 (m, 1H), 3.27 (m, 1H), 2.98-2.70 (m, 5H), 2.61 (q, J=7.6 Hz, 2H), 2.08 (m, 1H), 1.92-1.80 (m, 1H), 1.75-1.65 (m, 1H), 1.63-1.55 (m, 1H), 1.46-1.37 (m, 1H), 1.10 (t, J=7.6 Hz, 3H) ppm. 13C NMR (100 MHz, CDCl3) δ 152.1, 141.7, 140.4, 139.9, 136.4, 128.6, 127.5, 127.4, 126.4, 124.3, 123.2, 118.4, 115.9, 71.0, 54.3, 46.2, 45.3, 25.0, 24.2, 23.4, 18.3, 14.5 ppm. Purity: 100% LCMS (214 nm & 254 nm); retention time 1.61 min; (M+1) 351.

Provenance & Evidence