Cesium carbonate → 2-(4-(Trifluoromethyl)phenyl)isonicotinonitrile

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-chloro-4-pyridinecarbonitrile (0.50 g, 3.61 mmol), Cs2CO3 (1.70 g, 7.22 mmol) and 4-(trifluoromethyl)phenylboronic acid (0.82 g, 3.61 mmol) in dioxane (18 mL) was added palladium acetate (0.02 g, 0.07 mmol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.07 g, 0.14 mmol). The reaction vessel was sealed and heated to 100° C. for 4 hours and cooled to rt. The reaction mixture was filtered through a pad of celite, concentrated and purified by FCC (0%-100% EtOAc in hexane) to provide the desired product (0.69 g, 78%). MS (ESI): mass calcd. for C13H7F3N2, 248.2; m/z found 249.1 [M+H]+. 1H NMR (400 MHz, DMSO) δ 9.00-8.92 (m, 1H), 8.63-8.57 (m, 1H), 8.38 (d, J=8.1, 2H), 7.94-7.85 (m, 3H).

Provenance & Evidence