Cesium carbonate → 6-Chloro-4-[(4,6-dimethyl-2-pyridinyl)amino]-3-pyridinecarbonitrile

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Reaction Conditions

Reaction Steps

A mixture of 6-chloro-4-iodopyridine-3-carbonitrile (CAS: 1061357-83-2) (5.0 g, 19 mmol), 4,6-dimethylpyridin-2-amine (2.31 g, 18.9 mmol), Xantphos (2.2 g, 3.8 mmol), Pd2(dba)3 (1.73 g, 1.89 mmol), and cesium carbonate (8.62 g, 26.5 mmol) was purged with nitrogen. Dioxane (45 mL) was added, and the reaction mixture was heated to 50° C. After 1 hour, the mixture was allowed to cool to room temperature, filtered through a pad of CELITE, and washed with dichloromethane. The mixture was concentrated under reduced pressure, diluted with water, and extracted with dichloromethane (2×20 mL). The organics were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to provide 6-chloro-4-[(4,6-dimethylpyridin-2-yl)amino]pyridine-3-carbonitrile. MS ESI calc'd. for C13H12ClN4 [M+H]+ 259. found 259. 1H NMR (500 MHz, DMSO-d6) δ 9.70 (s, 1H), 8.57 (s, 1H), 8.31 (s, 1H), 6.92 (s, 1H), 6.80 (s, 1H), 2.37 (s, 3H), 2.25 (s, 3H).

Provenance & Evidence