Water → 1-(3-(Benzofuran-2-yl)pyridin-4-yl)ethanol

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Reaction Steps

A mixture of benzofuran-2-boronic acid (178 mg, 1.100 mmol), 1-(3-bromopyridin-4-yl)ethanol (202 mg, 1 mmol), sodium carbonate 2N in water (1 mL, 2.000 mmol), PdCl2(dppf).CH2Cl2 adduct (40.8 mg, 0.050 mmol) in DMF (5 mL) was heated to 100° C. for 3 hrs. The mixture was quenched with saturated NaHCO3 solution and extracted with EtOAc two times, dried over magnesium sulfate, filtered, concentrated. The residue was purified via Biotage (25M column, 20-60% EtOAc/heptane, v/v) giving the title compound (56 mg, 23%) as yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.56 (d, J=6.4 Hz, 3H), 5.53 (q, J=6.4 Hz, 1H), 7.03 (d, J=0.7 Hz, 1H), 7.31 (td, J=7.3, 0.9 Hz, 1H), 7.38 (td, J=8.0, 1.2 Hz, 1H), 7.54 (dd, J=8.2, 0.7 Hz, 1H), 7.66 (dd, J=7.6, 0.6 Hz, 1H), 7.85 (d, J=5.4 Hz, 1H), 8.63 (bs, 1H), 8.91 (bs, 1H). LC-MS (M+1) 240.2, t=1.25 min.

Provenance & Evidence