Cesium carbonate → HCID 25234253, compound

Participants

Reaction Steps

To a stirred solution of N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-2-trifluoromethyl-benzenesulfonamide (example 27, step 1, 44 mg) in N,N-dimethylacetamide (0.8 mL) were added cesium carbonate (45 mg), 2-bromomethyl-1,3-dioxolane (23 mg) and tetrabutylammonium iodide (3 mg). The mixture was stirred for 3 days at r.t. More tetrabutylammonium iodide (3 mg) and 2-bromomethyl-1,3-dioxolane (23 mg) were added and the mixture was stirred for 18 h at r.t. and for 24 h at 50° C. 2-Bromomethyl-1,3-dioxolane (23 mg) was added and the mixture was stirred for 5 h at 100° C. The mixture was diluted with ethyl acetate and washed with water. The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure. The product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 9:1 to 1:1) to give N-[1,3]dioxolan-2-ylmethyl-N-[5-(3-methanesulfonyl-phenyl)-thiophen-2-ylmethyl]-2-trifluoromethyl-benzenesulfonamide (34 mg) as a light yellow oil. MS: 578.6 ([M+NH4]+)

Provenance & Evidence