Triphenylphosphine → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(2-[3-(3-methyl-[1,2,4]oxadiazole-5-yl)phenyl]ethynyl)cyclohexan-1-one

Participants

Reaction Steps

A stirred mixture of 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethynylcyclohexan-1-one (0.200 g, 0.64 mmol) and 5-(3-iodophenyl)-3-methyl-[1,2,4]oxadiazole (0.201 g, 0.70 mmol) in dry triethylamine (4.6 mL) was treated under argon with a mixture of tetrakis(triphenylphosphine)palladium (0.032 g, 0.028 mmol), cuprous iodide (0.0067 g, 0.035 mmol), and triphenylphosphine (a small crystal) at 70° C. for 1 h and at 25° C. for 15 h. The reaction mixture was concentrated in vacuo and a solution of the residue was dissolved in methylene chloride, was treated with cold dilute hydrochloric acid and was dried over anhydrous sodium sulfate. The crude product was chromatographed (silica, 5 to 10% ethyl acetate in methylene chloride/hexanes 1:1) and the pure fractions were combined, concentrated in vacuo, crystallized from ethyl ether and dried at 60° C. in vacuo to afford the titled compound as an off-white powder (0.235 g, 78%), mp 88°-91° C. Anal. (C29H30N2O4) calcd: C 74.02, H 6.43, N 5.95, found: C 73.77, H 6.53, N 5.78.

Provenance & Evidence