Hydrochloric Acid → HCID 23502816, compound

Participants

Reaction Steps

A solution of 300 mg (0.495 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-(6-iodo-4-o-tolyl-pyridin-3-yl)-N-methyl-isobutyramide (Example 27) and 0.20 ml (0.59 mmol) 1-ethoxyvinyltri-n-butyltin in 1 ml toluene was deoxygenated by three freeze-thaw cycles. After addition of 17 mg (0.025 mmol) bis(triphenylphosphine)palladium(II) chloride the reaction mixture was heated at reflux for 16 h. Cooling to room temperature was followed by addition of 1 ml 2 M aqueous hydrochloric acid solution. After 15 min 2 ml 1N aqueous sodium hydroxide solution and 35 mg (0.59 mmol) potassium fluoride were added, followed by extraction with four portions of ethyl acetate. The combined organic layers were washed with brine, dried with magnesium sulfate and concentrated. Column chromatography afforded 147 mg (57%) of the title compound as a colorless gum.

Provenance & Evidence