Dimethylamine → HCID 68850320, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromo-3-(morpholinosulfonyl)-N-((1S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)benzamide (2.4.AaBa, 0.400 g, 0.824 mmol), dimethylamine (Cd, 2 mL 2M in THF), and 3 mL N,N-dimethylformamide were mixed. Tris(dibenzylideneacetone)dipalladium(0) (0.08 g, 0.08 mmol), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.05 g, 0.08 mmol), and potassium tert-butoxide (0.9 g, 8 mmol) were then added. The reaction was heated to at 100° C. for 24 hours. After aqueous workup and acidic extraction, the organic layer was evaporated to yield a yellow solid. The product was then purified by SiO2 chromatography (5-20% ethyl acetate/hexane) to yield 4-(dimethylamino)-3-(morpholinosulfonyl)-N-((1S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)benzamide (2E) as an off-white solid (180 mg, 49% yield). MS analysis (m+1)=450.6.

Provenance & Evidence