Sodium Carbonate → 3,2'-Difluoro-5'-(7-trifluoromethyl-[1,8]naphthyridin-4-yl)biphenyl-2-carbonitrile

Participants

Reaction Steps

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol), 5′-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-3,2′-difluorobiphenyl-2-carbonitrile (91 mg, 0.28 mmol), tetrakis(triphenylphosphine)palladium(0) (5.0 mg, 2 mol %) and 2 M sodium carbonate solution (0.5 mL, 1.0 mmol) in DME (3 mL) was irradiated in a microwave reactor at 150° C. for 10 min. The mixture was cooled to room temperature and was diluted with water (3 mL) and dichloromethane (3 mL), and was then filtered through a PTFE cartridge. The separated organic phase was concentrated in vacuo, and the crude product was recrystallised from ethyl acetate, then again from ethyl acetate/isohexane, yielding 3,2′-difluoro-5′-(7-trifluoromethyl-[1,8]naphthyridin-4-yl)biphenyl-2-carbonitrile as an off-white solid (26 mg, 30%). δH (360 MHz, CDCl3) 7.29-7.33 (1H, m), 7.41 (1H, d, J 7.4), 7.48 (1H, t, J 8.9), 7.58-7.61 (3H, m), 7.67-7.73 (1H, m), 7.89 (1H, d, J 8.8), 8.68 (1H, d, J 8.8), 9.29 (1H, dd, J 2.8 and 1.4). m/z (ES+) 412 [MH]+.

Provenance & Evidence