Acetonitrile → HCID 70125162, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a mixture of 4-bromo-1,2-(methylenedioxy)benzene (1.20 g, 5.97 mmol), N-methyl-N-(tert-butoxycarbonyl)-4-penten-2-amine (1.19 g, 5.97 mmol), palladium(II) acetate (13.5 mg, 0.06 mmol), tri-o-tolylphosphine (73.1 mg, 0.24 mmol), triethylamine (1.7 mL, 11.9 mmol) and anhydrous acetonitrile (3.4 mL) was stirred and heated under reflux at 80-85° C. (oil bath temperature) for 22 h. The resulting mixture, containing brown solids, was cooled to ambient temperature, diluted with water (25 mL), and extracted with CHCl3 (3×25 mL). The combined CHCl3 extracts were dried (Na2SO4), filtered, concentrated by rotary evaporation and dried under high vacuum to produce an orange-yellow oil (2.13 g). The crude product was purified by column chromatography on silica gel (100 g), eluting with ethyl acetate-hexane (15:85, v/v). Selected fractions containing the product (Rf 0.33) were combined, concentrated by rotary evaporation and the residue was vacuum dried to give 1.08 g (56.6%) of a light-yellow oil.

Provenance & Evidence