Cyclohexylamine → Benzyl 4-cyano-3-(cyclohexylamino)benzoate

Participants

Reaction Conditions

Reaction Steps

To a pressure vessel were added benzyl 3-bromo-4-cyanobenzoate (150 mg, 0.47 mmol) prepared as described in example 11 (steps 1, 2), cesium carbonate (310 mg, 0.95 mmol), cyclohexylamine (108 uL, 0.95 mmol), XANTPHOS (27 mg, 0.047 mmol), tris(dibenzylideneacetone)dipalladium(0) (21 mg, 0.023 mmol), and dioxane (3 mL). The vessel was sealed and heated to 95° C. for 4 h. After cooling to room temperature, the mixture was diluted with ethyl acetate and was washed with water. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography (10% ethyl acetate in hexanes) to provide benzyl 4-cyano-3-(cyclohexylamino)benzoate (118 mg, 0.35 mmol, 75% yield) as a yellow syrup. 1H NMR (400 MHz, CDCl3): 7.45-7.30 (m, 7H), 7.27 (dd, 1H), 5.36 (s, 2H), 4.56 (d, 1H), 3.48-3.38 (m, 1H), 2.08-2.01 (m, 2H), 1.83-1.75 (m, 2H), 1.71-1.64 (m, 1H), 1.46-1.35 (m, 2H), 1.31-1.20 (m, 3H); MS (EI) for C21H22N2O2: 333 (M−H).

Provenance & Evidence