Cesium carbonate → 2-Chloro-N-((1-hydroxycycloheptyl)methyl)-5-[1-(2-hydroxyethyl)-5-methyl-1H-pyrazol-3-yl]benzamide

Participants

Reaction Steps

A mixture of 2-chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(5-methyl-1H-pyrazol-3-yl)-benzamide (5.0 g, 13.8 mmol) and cesium carbonate (9.0 g, 27.7 mmol) in dimethylsulfoxide (50 mL) was stirred at room temperature for 10 minutes. Bromoethanol (1.9 g, 15.2 mmol) was added and the resulting mixture was stirred at 80° C. for 12 h. The mixture was cooled to room temperature and filtered. The filtrate was diluted with ethyl acetate (300 mL), washed with water and brine, dried, filtered and concentrated in vacuo. The residue was triturated with dichloromethane-ethyl acetate-diethyl ether (1:1:1, 100 mL) and washed with ethyl acetate to afford the title compound (3.3 g). LCMS (m/z) 406.1 M+1.

Provenance & Evidence