3-Hydroxypyridine → 4-(Pyridine-3-yloxy)-2-methoxybenzaldehyde

Participants

Reaction Steps

4-Bromo-2-methoxybenzaldehyde (1.00 g, 4.65 mmol), cesium carbonate (3.03 g, 9.30 mmol), 3-hydroxypyridine (0.884 g, 9.30 mmol), cuprous chloride (0.230 g, 2.325 mmol), 2,2,6,6-tetramethyl-3,5-heptanedione (0.214 g, 1.163 mmol) in NMP (11.6 mL) in a sealed microwave vial was heated to 120° C. overnight in an oil bath. The reaction vessel was allowed to cool before water was added to dilute the mixture; EtOAc was then added to extract the product. The organic phase was separated and washed with water (2×) and brine (1×) before being dried with Na2SO4 and evaporated to afford an oil. This material was chromatographed on silica 0-80% EtOAc in hexanes to yield 4-(pyridine-3-yloxy)-2-methoxybenzaldehyde (0.665 g) as a solid.

Provenance & Evidence