Cesium fluoride → 2-(4-Cyanonaphthalene-2-yl)isonicotinic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-cyano-2-naphthaleneboronic acid (0.10 g), 2-bromoisonicotinic acid ethyl ester (0.12 g) and cesium fluoride (0.09 g) in dimethoxyethane (6 mL) was added tetrakis(triphenylphosphine)palladium (0.06 g), and the mixture was stirred at 150° C. for 40 minutes using microwave reactor (Biotage). The reaction mixture was filtered through a Celite pad, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0-66/34) to give 2-(4-cyanonaphthalene-2-yl)isonicotinic acid ethyl ester (0.14 g). To a solution of this compound (0.14 g) in a mixed solvent of tetrahydrofuran (4 mL), ethanol (1 mL) and water (1 mL) was added lithium hydroxide monohydrate (0.060 g), and the mixture was stirred at room temperature overnight. To the reaction mixture was added acetic acid (0.27 mL). The precipitated solid was collected by filtration, and washed with water and n-hexane. The solid was dried under reduced pressure to give the title compound (0.098 g).

Provenance & Evidence