Phenylacetylene → HCID 12018748, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 4-{2-bromo-4-[3-(pyridin-2-ylamino)propoxy]phenyl}-3,3-dimethylbutanoate (500 mg) was dissolved in Et3N (5 ml) followed by the addition of phenylylacetylene (250 μL), Cul (11 mg), triphenylphosphine (85 mg), and Pd(Ph3P)2Cl2 (42 mg). The reaction mixture was heated to 80° C. under a nitrogen atmosphere for 24 hours. Further phenylacetylene (125 μL) and triethylamine (5 mL) were added and heating was continued for a further 24 h. The mixture was cooled to room temperature, diluted with ethyl acetate (50 mL) and filtered through a pad of celite. The solvent was evaporated and the residue was chromatographed on silica gel eluting with hexane/ethyl acetate (3:2). This gave the product (516 mg) as an oil. The NMR spectrum was consistent for the proposed structure.

Provenance & Evidence