Diisopropylamine → HCID 86633520, compound

Participants

Reaction Steps

In nitrogen atmosphere, ethyl [4-(2,6-dibromopyridine-4-ylsulfanyl)-2-methylphenoxy]acetate (110 mg, 0.239 mmol; prepared as described in example 6) and 2-ethynylpyridine (74 mg, 0.717 mmol) were dissolved in degassed anhydrous tetrahydrofuran (2 mL). A 0.15 M Solution of tri-tert-butylphosphine in cyclohexane (0.191 mL, 0.029 mmol) was added via syringe. Copper(I) iodide (1.9 mg, 0.010 mmol), dichloro(bisbenzonitrile)palladium (5.5 mg, 0.014 mmol) and diisopropylamine (80 μL, 0.574 mmol) were subsequently added. The traces of air were removed and the mixture was stirred under nitrogen at ambient temperature 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 9:1-1:9) yielding ethyl [4-[2,6-bis[(2-pyridyl)ethynyl]pyridine-4-ylsulfanyl]-2-methylphenoxy]acetate as a brown oil beside of a by-product-mono substituted derivative, ethyl [4-[6-bromo-2-[(2-pyridyl)ethynyl]pyridine-4-ylsulfanyl]-2-methylphenoxy]acetate (50 mg, 22% yield).

Provenance & Evidence