HCID 86688721, compound → HCID 86688720, compound

Participants

Reaction Steps

4-Fluoro-N-(5-(4,4,4-trifluoro-3-hydroxybutyl)-1,2,3,4-tetrahydronaphthalen-2-yl)benzenesulfonamide, designated as 23 in FIG. 7, was prepared as follows. A mixture of 4-fluoro-N-(5-(3-hydroxypropyl)-1,2,3,4-tetrahydronaphthalen-2-yl)benzenesulfonamide (70 mg, 0.19 mmol) and pyridinium chlorochromate (60 mg, 0.28 mmol) in anhydrous dichloromethane (3 mL) was stirred at room temperature for 1 hour. The reaction mixture was filtered through a pad of celite, and the solvent was evaporated. The residue was purified by a short silica gel column chromatography using ethyl acetate-hexanes 2:3 as eluent to give 4-fluoro-N-(5-(3-oxopropyl)-1,2,3,4-tetrahydronaphthalen-2-yl)benzenesulfonamide (20) that was dissolved in anhydrous tetrahydrofuran (1 mL) and cooled to 0 C. Tetrabutylammoniumfluoride in THF (5 μL, 1 M, 0.004 mmol) was added followed by trifluoromethyl trimethylsilane (30 mg, 33 μL, 0.21 mmol). The reaction was warmed to room temperature and stirred overnight. Hydrochloric acid (1 M, 1.5 mL) was added and stirring continued at room temperature for 1.5 hour. The aqueous layer was extracted with dichloromethane, dried over magnesium sulfate and concentrated to dryness. Silica gel chromatography (30% ethyl acetate in hexanes) gave the purified product as colorless oil. Yield: 13%.

Provenance & Evidence