Cesium carbonate → HCID 123573018, compound

Participants

Reaction Steps

To a round-bottomed flask charged with 5-(5-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)-1H-pyrazol-3-yl)-3-(trifluoromethoxy)pyridin-2-amine (0.40 g, 0.35 mmol) and cesium carbonate (0.68 g, 2.1 mmol) in N,N-dimethylformamide (4 mL) was added bromomethylcyclopropane (0.28 mg, 2.1 mmol) at 20° C. After 16 h, the reaction mixture was partitioned between ethyl acetate (20 mL) and water (10 mL). The aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organics were washed with saturated aqueous sodium chloride solution (2×10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (30% ethyl acetate in petroleum ether) afforded product as an orange oil (0.30 g, 69% yield). LCMS (ESI) [MH]+=633.1.

Provenance & Evidence