Diisopropylamine → HCID 86633518, compound

Participants

Reaction Conditions

Reaction Steps

In nitrogen atmosphere, ethyl [4-(3,5-dibromophenylsulfanyl)-2-methylphenoxy]-acetate (460 mg, 1 mmol; prepared as described in example 1) and 2-ethynylpyridine (110 μL, 1.1 mmol) were dissolved in anhydrous tetrahydrofuran (7 mL). 0.15 M Solution of tri-tert-butylphosphine in cyclohexane (0.6 mL, 0.06 mmol) was added via syringe. Copper(I) iodide (3.8 mg, 0.02 mmol), dichloro(bisbenzonitrile)palladium (11 mg, 0.03 mmol) and diisopropylamine (155 μL, 1.1 mmol) were added. Traces of the air were removed and mixture was stirred under nitrogen at 40° C. overnight. 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 90:10-85:15) yielding ethyl [4-[3-bromo-5-[(pyridin-2-yl)ethynyl]phenylsulfanyl]-2-methylphenoxy]acetate beside of 144 mg (30%) of unchanged starting dibromo derivative.

Provenance & Evidence