Sodium hydride → HCID 68915051, compound

Participants

Reaction Steps

In an inert atmosphere (argon), allyl-((S)-6-bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester (1.94 g, 5.3 mmol) was dissolved in trifluortoluol (10 ml) at room temperature. Tris(dibenzylideneacetone)dipalladium (230 mg, 0.25 mmol) and tri-tert-butyl-phosphane (152 mg, 0.75 mmol) were added to the reaction mixture. In a separate flask, 4-Isopropyl-benzenesulfonamide (996 mg, 5 mmol) was dissolved in trifluortoluol (20 ml) at 65° C. Sodium hydride (50% in oil) (240 mg, 5 mmol) was added, stirred for 5 minutes and added to the reaction mixture. The reaction mixture was dispensed into 8 vials and stirred for 1 hour at 150° C. in the microwave (CEM). The combined reaction mixture was evaporated to dryness. H20 (50 ml) was added and extracted three times with 50 ml diethylether. The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness to yield 4.3 g of crude product. The crude product was purified with silica gel chromatography with cyclohexane/ethyl acetate (85:15) as eluent, yielding the product (1.5 g, 50% purity, 31% yield).

Provenance & Evidence