Sodium Carbonate → 5-(3'-Chloro-6-fluorobiphenyl-3-yl)-2-trifluoromethyl[1,8]naphthyridine

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Reaction Steps

A mixture of trifluoromethanesulfonic acid 2-fluoro-5-(7-trifluoromethyl-[1,8]naphthyridin-4-yl)phenyl ester (30.0 mg, 0.068 mmol), 3-chlorobenzeneboronic acid (13.9 mg, 0.089 mmol), dichlorobis-(triphenylphosphine)palladium(II) (5.0 mg, 7.1 μmol) and 2 M sodium carbonate solution (0.5 mL) in DME (3 mL) was irradiated in a microwave reactor at 150° C. for 10 min. After cooling to room temperature, the mixture was diluted with dichloromethane (3 mL) and water (3 mL), and was filtered through a PTFE cartridge. The separated organic phase was concentrated in vacuo, and the residual material was purified by preparative thin layer chromatography on silica gel, eluting with 5% ethyl acetate in dichloromethane, affording 5-(3′-chloro-6-fluorobiphenyl-3-yl)-2-trifluoromethyl[1,8]naphthyridine as a white solid (12.7 mg, 46%). δH (360 MHz, CDCl3) 7.33-7.50 (5H, m), 7.57 (1H, dd, J 1.8 and 7.0), 7.59-7.60 (2H, m), 7.84 (1H, d, J 8.8), 8.54 (1H, d, J 8.8), 9.29 (1H, d, J 4.2). m/z (ES+) 403, 405 [MH]+.

Provenance & Evidence