Triethylamine → HCID 80033541, compound

A solution of 2-thiophenecarbonyl chloride (3.0 g, 23.41 mmol) in anhydrous dioxane (60 mL) was bubbled with argon for 10 minutes. Triethylamine (9.80 mL, 70.22 mmol) was added and the bubbling was maintained for 5 minutes. Bis(triphenylphosphine)palladium(II) dichloride (657 mg, 0.94 mmol), copper iodide (356 mg, 1.87 mmol) and 3,3-diethoxy-1-propyne (3.36 mL, 23.41 mmol) were added, and the reaction mixture was stirred for 2 hours at room temperature, under argon atmosphere. The solution was filtered and water (50 mL) was added to the filtrate. Layers were separated and the aqueous layer was extracted with dichloromethane (2×50 mL). The combined organic layers were washed with a saturated solution of sodium hydrogenocarbonate (50 mL), dried over sodium sulfate and concentrated in vacuo. The residue was dissolved in ethanol (200 mL) and hydrazine hydrate (2.51 g, 35.10 mmol) was added. The reaction mixture was stirred overnight and concentrated in vacuo. The residue was dissolved in ethyl acetate (40 mL) and successively washed with water (40 mL) and brine (40 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to provide 5-(diethoxymethyl)-3-(thiophen-2-yl)-1H-pyrazole (34a) (4.39 g, 17.40 mmol, 74%) which was used without further purification.

1. temperaturethe bubbling was maintained for 5 minutes
2. filtrationThe solution was filtered
3. additionwater (50 mL) was added to the filtrate
4. customLayers were separated
5. extractionthe aqueous layer was extracted with dichloromethane (2×50 mL)
6. washThe combined organic layers were washed with a saturated solution of sodium hydrogenocarbonate (50 mL)
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated in vacuo
9. dissolutionThe residue was dissolved in ethanol (200 mL)
10. stirringThe reaction mixture was stirred overnight
11. concentrationconcentrated in vacuo
12. dissolutionThe residue was dissolved in ethyl acetate (40 mL)
13. washsuccessively washed with water (40 mL) and brine (40 mL)
14. dry with materialThe organic layer was dried over sodium sulfate
15. concentrationconcentrated in vacuo

ORD record

ord-f950d322fa644806b79d8b0fe4629a21

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260395B2