Cesium carbonate → (S)-isopropyl 7-cyano-4-(3-fluoro-2-methoxybenzyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamate

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Reaction Steps

A solution of (S)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamic acid isopropyl ester (1.50 g, 5.29 mmol) and 1-(chloromethyl)-3-fluoro-2-methoxybenzene (1.11 g, 6.35 mmol) in N,N-dimethylformamide (10 mL) is treated with cesium carbonate (2.59 g, 7.94 mmol) at room temperature and stirred overnight under nitrogen. The reaction mixture is diluted with water and ether/hexanes. The white solids that crash out of solution are filtered, rinsed with water, ether, hexanes, and dried under vacuum at 50° C. for 48 h to obtain the title compound as a white solid (2.18 g, 98%). LC-ES/MS m/z 422.2 [M+H]+, TR=4.57 min.

Provenance & Evidence