Cesium carbonate → 4-Pyridinecarbonitrile, 2-methoxy-6-[4-(trifluoromethyl)phenyl]-

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Reaction Conditions

Reaction Steps

The nitrile 25F (2.3 g, 13.8 mmol), 4-trifluoromethylphenylboronic acid (2.61 g, 1.1 mol eq), palladium acetate (62 mg, 0.02 mol eq), cesium carbonate (8.97 g, 2 mol eq), and XPhos (260 mg, 0.04 mol eq) were mixed, placed under a nitrogen atmosphere and dioxane (10 mL) was added. The mixture was heated at 100° C. for 4 h. After cooling, the mixture was filtered through a celite pad, washed with dioxane (2×30 mL) and concentrated under reduced pressure. The residue was purified by flash chromatography (9:1 petroleum ether:EtOAc) to afford 26I as a pale yellow solid (840 mg, 25% Yield). 1HNMR (DMSO, 200 MHz) δ 4.03 (s, 3H), 7.46 (s, 1H), 7.90 (d, 2H, J=7.8), 8.17 (s, 1H), 8.40 (d, 2H, J=8).

Provenance & Evidence