Sodium Carbonate → HCID 58585876, compound

Participants

Reaction Steps

To the solution of 4-chloro-3-methanesulfonyl-quinoline-6-carboxylic acid ethyl ester (example 61f, 200 mg, 0.64 mmol) in DME (8 mL), phenylboronic acid (116 mg, 0.96 mmol), a catalytical amount of tetrakis(triphenylphosphine)-palladium(0) (147 mg, 0.13 mmol), and sodium carbonate solution (2 M, 1.12 ml, 2.23 mmol) were added. The resulted solution was heated under the microwave irradiation at 150 degrees for 15 min. After cooling to room temperature, the reaction mixture was filtered through a bed of celite with DME. The filtrate was quenched with water, and then extracted with ethyl acetate. The organic layers were collected, washed with brain, dried over sodium sulfate, and then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 30%-50% ethyl acetate in hexane in 15 min, then 50% ethyl acetate in hexane in 9 min) afforded 3-methanesulfonyl-4-phenyl-quinoline-6-carboxylic acid ethyl ester (159 mg, 70%). LC-MS m/e 356 (MH+).

Provenance & Evidence