Sodium Carbonate → (1S)-1-(2-{[6-(2-Fluorophenyl)-2-naphthyl]sulfonyl}phenyl)ethanol

Participants

Reaction Conditions

Reaction Steps

A mixture of (1S)-1-{2-[(6-bromo-2-naphthyl)sulfonyl]phenyl}ethanol [Example 10 Step 2] (102 mg, 0.26 mmol), 2-fluorophenylboronic acid (75 mg, 0.53 mmol), palladium(II) acetate (3 mg, 0.013 mmol), tri(o-tolyl)phosphine (9 mg, 0.028 mmol), sodium carbonate (83 mg, 0.787 mmol) and water (0.5 mL) in 1,2-dimethoxyethane (3 mL) was degassed and stirred at 80° C. (oil bath temperature) under nitrogen for 16 hours. The cooled reaction mixture was diluted with ethyl acetate and filtered. The filtrate was evaporated and the residue purified by flash chromatography, eluting with 60-75% diethyl ether/isohexane, to afford the title compound as a foam (86 mg, 81%). 1H NMR (500 MHz, CDCl3) δ 8.56 (1H, s), 8.17 (1H, dd, J 1.0, 8.0 Hz), 8.06 (2H, m), 7.98 (1H, d, J 8.6 Hz), 7.83 (1H, m), 7.77 (2H, m), 7.66 (1H, t, J 7.5 Hz), 7.54 (1H, dt, J 1.6, 7.7 Hz), 7.49 (1H, t, J 7.7 Hz), 7.42-7.38 (1H, m), 7.28 (1H, m), 7.21 (1H, m), 5.68-5.62 (1H, m), 2.51 (1H, d, J 3.2 Hz), 1.36 (3H, d, J 6.3 Hz); m/z (ES+) 389 [(M-OH)+].

Provenance & Evidence