Triethylamine → HCID 67052477, compound

Participants

Reaction Conditions

Reaction Steps

4-bromopyridine hydrochloride (194 mg, 1 mmol), phenylpent-1-en-4-yn-3-ol (190 mg, 1.2 mmol), bis(triphenylphosphine)palladium(II) dichloride (14 mg, 0.02 mmol), copper iodide (3 mg, 0.03 mmol) and triphenylphosphine (52 mg, 0.2 mmol) were introduced in a 10 mL microwave vial flushed with argon. This was diluted with anhydrous triethylamine (900 μL, 4 mmol) in anhydrous degased 1,4-dioxane (1.1 mL). The solution was heated under microwave irradiation at 120° C. for 45 min. The reaction mixture was diluted with chloroform (15 mL) and extracted with a 1M aqueous solution of hydrochloric acid (3×20 mL). The aqueous was next basified with an aqueous solution of sodium hydroxide (5M, 20 mL). Product was extracted with ethyl acetate (3×40 mL). The combined organic layers were dried over magnesium sulfate, filtered, and evaporated to dryness to give crude product which was purified by flash chromatography (SiO2, 70% ethyl acetate in hexanes) to give the desired product as a free base. This was dissolved in 1,4-dioxane (15 mL) and hydrogen chloride 1.25M in ethanol (2 mL) was added. The suspension was filtered to recover the hydrochloric salt of the final compound TG011A96 (115 mg, 42%) as a fine yellow powder.

Provenance & Evidence