Potassium Acetate → {3-[(4-methoxybenzyl)oxy]-4-oxo-4H-1,2'-bipyridin-4'-yl}boronic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 4′-iodo-3-[(4-methoxybenzyl)oxy]-4H-1,2′-bipyridin-4-one (5.6 g, 12.9 mmol), bis(pinacolato)diboron (4.91 g, 19.3 mmol), KOAc (2.53 g, 25.8 mmol), and Pd(dppf)Cl2 (0.6 g) in 1,4-dioxane (100 mL) was heated to 100° C. overnight. After cooling to room temperature, the reaction mixture was concentrated to give a residue which was purified by Prep-HPLC to give {3-[(4-methoxybenzyl)oxy]-4-oxo-4H-1,2′-bipyridin-4′-yl}boronic acid. 1H NMR (DMSO, 400 MHz) δ 8.61(s, 1H), 8.51 (d, J=4.4 Hz, 1H), 8.437 (dd, J=8.0, 2.0 Hz, 1H), 8.21 (d, J=2.4 Hz, 1H), 8.00 (s, 1H), 7.65 (d, J=4.8 Hz, 1H), 7.36 (d, J=8.4 Hz, 2H), 6.92 (d, J=8.4 Hz, 2H), 6.34(d, J=7.6 Hz, 1H), 4.98 (s, 2H), 3.72 (s, 3H). MS (M+H)+ 353.2.

Provenance & Evidence