3-Butyn-1-OL → RWJ 67657

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-(4-fluorophenyl)-2-iodo-1-(3-phenylpropyl)-5-(4-pyridyl)imidazole (1.42 g, 2.74 mmol) and 3-butyn-1-ol (0.289 g, 4.1 mmol) in diisopropylamine (10 mL) was added bis(acetato)-bis(triphenylphosphine) palladium (0.102 g, 0.14 mmol), followed by the addition of copper(I) iodide (0.052 g, 0.274 mmol). The mixture was stirred at 75° C. for 4 h. The reaction mixture was then cooled to room temperature and quenched with water (100 mL). The mixture was extracted with ethyl acetate (2×50 mL). The combined ethyl acetate extract was washed with water (2×30 mL), brine (30 mL), and dried with Na2SO4. After removal of solvents, the crude product was obtained as a brown solid.

Provenance & Evidence