Diisopropylamine → HCID 10378725, compound

Participants

Reaction Steps

Preparation of compound 26(a) (acetic acid 4-cyano-2-phenylethynyl-phenyl ester). 1,4-Dioxane (2.5 mL, dry) was added to a stirred suspension of CuI (8.0 mg, 2 mol %) and dichlorobis(benzonitrile)palladium (II) (24 mg, 3 mol %) in a dry septum-capped flask with constant purging of argon. Tri-t-butylphosphine (542 μl, 0.25M solution in 1,4-dioxane), diisopropyl amine (350 μl, 4.17 mmol), acetic acid 2-bromo-4-cyano-phenyl ester (500 mg, 2.08 mmol), and phenyl acetylene (254 mg, 2.71 mmol) were added with syringes to the stirred reaction mixture. The reaction mixture was stirred for 6 hours, and then diluted with ethyl acetate and passed through small pad of silica gel. The filtrate was concentrated, and the crude product was purified by column chromatography (silica gel, 5 to 20% ethyl acetate in hexanes) to provide 390 mg (72%) of the desired product.

Provenance & Evidence