Cesium carbonate → HCID 178468908, compound

Participants

Reaction Steps

A mixture of ethyl 3-bromo-4-cyanobenzoate (0.82 g, 3.24 mmol), 1,1-dimethylethyl(trans-4-aminocyclohexyl)carbamate (0.69 g, 3.24 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.148 g, 0.16 mmol), XANTPHOS (0.19 g, 0.32 mmol) and cesium carbonate (1.48 g, 4.54 mmol) in dioxane (13 mL) was refluxed for 15 hours. On cooling to room temperature, the mixture was filtered through Celite, concentrated, and purified by silica gel column chromatography using hexanes:ethyl acetate from 5:1 to 4:1 to afford ethyl 4-cyano-3-{[trans-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)cyclohexyl]amino}benzoate (0.370 g, 30% yield). 1H NMR (400 MHz, d6-DMSO): 7.59 (d, 1H), 7.28 (s, 1H), 7.13 (dd, 1H), 6.82 (d, 1H), 6.05 (d, 1H), 4.31 (q, 2H), 3.46-3.37 (m, 1H), 3.28-3.17 (m, 1H), 1.95-1.85 (m, 2H), 1.84-1.76 (m, 2H), 1.46, 1.22 (m, 16H).

Provenance & Evidence