Triethylamine → HCID 67052477, compound

Temperature

120 °C

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.

1. customvial flushed with argon
2. customin anhydrous degased 1,4-dioxane (1.1 mL)
3. additionThe reaction mixture was diluted with chloroform (15 mL)
4. extractionextracted with a 1M aqueous solution of hydrochloric acid (3×20 mL)
5. extractionProduct was extracted with ethyl acetate (3×40 mL)
6. dry with materialThe combined organic layers were dried over magnesium sulfate
7. filtrationfiltered
8. customevaporated to dryness
9. customto give crude product which
10. customwas purified by flash chromatography (SiO2, 70% ethyl acetate in hexanes)

ORD record

ord-51fab5b41a1e4c79b51e40d1b55ddf34

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174960B2