Diisopropylamine → HCID 86633516, compound

Participants

Reaction Steps

In nitrogen atmosphere, ethyl [4-(3,5-dibromophenylsulfanyl)-2-methylphenoxy]-acetate (138 mg, 0.30 mmol; prepared as described in example 1) and 2-ethynylpyridine (80 μL, 0.80 mmol) were dissolved in anhydrous tetrahydrofuran (4 mL). 0.15 M Solution of tri-tert-butylphosphine in cyclohexane (0.2 mL, 0.03 mmol) was added via syringe. Copper(I) iodide (1.9 mg, 0.01 mmol), dichloro(bisbenzonitrile)palladium (5.7 mg, 0.015 mmol) and diisopropylamine (112 μL, 0.80 mmol) were added. Traces of the air were removed and mixture was stirred under nitrogen at ambient temperature overnight and then at 50° C. for 1 h. The mixture was diluted with ethyl acetate (10 mL) and filtered through a short path of silica gel. The filtrate was concentrated and purified by column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 7:3-1:1-3:7) yielding ethyl [4-[3,5-bis-[(pyridin-2-yl)ethynyl]-phenylsulfanyl]-2-methylphenoxy]acetate.

Provenance & Evidence