Cesium carbonate → HCID 24985290, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1H-indole-5-carbonitrile (0.05 g, 0.35 mmol) in anhydrous DMF (2 mL) was added Cs2CO3 (0.18 g, 0.55 mmol) and 3-(chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole (0.14 g, 0.55 mmol). The mixture was heated at 90° C., under N2, for 30 min. Upon cooling, the mixture was partitioned between Et2O and H2O. The aqueous phase was extracted with Et2O (×2). The combined organic phases were washed with sat'd brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (2-20% EtOAc-hexanes gradient) and the product crystallized from CH2Cl2-hexanes to afford the title compound as a white solid (0.1 g, 78% yield): MS (ES) m/z 369 (M+1).

Provenance & Evidence