Cesium carbonate → [6-Chloro-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-(4-cyclopropanecarbonyl-piperazin-1-yl)-methanone

Participants

Reaction Steps

To a mixture of [6-chloro-5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]-piperazin-1-yl-methanone (example 36, 150 mg, 1.0 eq.) and cesium carbonate (243 mg, 2.0 eq.) in acetonitrile (8 mL) was added cyclopropane carbonylchloride. The reaction mixture was refluxed 4 h. The reaction mixture was concentrated in vacuo and the residue partitioned between tert-butylmethylether and water. The aqueous layer was extracted with tert-butylmethylether and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo. The residue was purified by flash chromatography on silica gel with a 98:2 to 95:5:0.25 gradient of dichloromethane/methanol/ammonia as eluant, to afford 59 mg (46%) of the title compound as a light-yellow solid.

Provenance & Evidence