Dichloromethane → 1-(3-Fluoro-5-(6-methoxynaphthalen-2-yl)pyridin-4-yl)ethanol

Participants

Reaction Steps

A mixture of 6-methoxynaphthalen-2-ylboronic acid (333 mg, 1.650 mmol), 1-(3-bromo-5-fluoropyridin-4-yl)ethanol 4a (330 mg, 1.5 mmol), sodium carbonate (2M in water, 1.5 mL, 3.00 mmol), PdCl2(dppf).CH2Cl2 adduct (61.2 mg, 0.075 mmol) in DMF (6 mL) was heated to 100° C. for 2 hrs. The mixture was quenched with sat NaHCO3 and extracted with EtOAc two times, dried over magnesium sulfate, filtered, concentrated. The residue was purified via Biotage (20-60% EtOAc/heptane; SNAP25 column) giving the title compound (227 mg, 51%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.62 (dd, J=6.7, 1.0 Hz, 3H), 3.96 (s, 3H), 4.99 (q, J=6.7 Hz, 1H), 7.19-7.26 (m, 2H), 7.36 (dd, J=8.4, 1.7 Hz, 1H), 7.70 (s, 1H), 7.78 (d, J=8.9 Hz, 1H), 7.83 (d, J=8.5 Hz, 1H), 8.40 (s, 1H), 8.48 (d, J=2.7 Hz, 1H). LC-MS (M+1) 298.0, t=1.49 min.

Provenance & Evidence