4-Fluorophenylboronic acid → HCID 11740960, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4,2′-difluoro-5′-(3-methylsulfanyl-[1,2,4]triazin-5-yl)biphenyl-2-carbonitrile (0.11 g, 0.32 mmol), cuprous 3-methylsalicylate (0.153 g, 0.711 mmol) and 4-fluorobenzeneboronic acid (0.1 g, 0.711 mmol) in dry THF (8 ml) was added tetrakis(triphenylphosphine)palladium(0) (0.037 g, 0.032 mmol) and the mixture heated at 50° C. for 5 h. The reaction was allowed to cool to ambient temperature, diluted with DCM (20 ml) and filtered through a glass fibre filter. The dark brown solution was evaporated to give a brown solid. The crude product was chromatographed on silica (eluted with 3% MeOH in DCM) to give the product as a yellow solid. Recrystallisation from DCM/MeOH gave the title compound as a pale yellow solid (52 mg): δH (400 MHz, CDCl3) 7.24 (2H, m), 7.44-7.49 (2H, m), 7.55-7.62 (2H, m), 8.36-8.39 (2H, m), 8.64-8.69 (2H, m), 9.62 (1H, s); m/z (ES+) 389 (M++H).

Provenance & Evidence