Sodium hydride → tert-butyl cis-3-fluoro-4-((4-(N-isobutyl-N-(5-isopropylpyridin-2-yl)sulfamoyl)phenoxy)methyl)piperidine-1-carboxylate

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Reaction Steps

4-fluoro-N-isobutyl-N-(5-isopropylpyridin-2-yl)benzenesulfonamide (30 mg, 0.10 mmol) was dissolved in N,N-dimethylformamide (DMF) (3 mL) and to this solution was added sodium hydride (2 mg, 0.10 mmol, 60% wt in mineral oil) followed by tert-butyl cis-3-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate (24 mg, 0.10 mmol). The reaction was stirred for 3 hours at room temperature, under nitrogen, then quenched with water and concentrated in vacuo. The crude product was extracted to the organic phase of an aqueous workup between ethyl acetate and water. The organic phase was then passed through a hydrophobic frit and concentrated in vacuo to give the title compound (47 mg). LCMS (2 min, formic) Rt 1.50 min, m/z (ES+) 564 (M+H).

Provenance & Evidence