Ethyl acetate hexane → HCID 178506085, compound

Temperature

60 °C

In a 10 mL seal tube, 2,6-bis(trifluoromethyl)-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)pyridine (2) (0.15 g, 1 eq.) was dissolved in dioxane HCl (5 mL) and seal tube was heated to 60° C. for 6 h. Reaction completion was monitored on TLC using ethyl acetate:hexane (5:5) as mobile phase. The reaction mixture was quenched into the ice-water NaHCO3 solution (50 mL) and was extracted with ethyl acetate (3×50 mL). Organic layer was washed with brine solution (3×50 mL). The organic layer was dried using anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide the 0.3 g of crude compound. The compound was purified by column chromatography using ethyl acetate/hexane as mobile phase. Compound was eluted out at 30% ethyl acetate in hexane to afford 4-(1H-1,2,4-triazol-3-yl)-2,6-bis(trifluoromethyl)pyridine (3) 0.060 g. Yield: 58.4%.

1. customIn a 10 mL seal tube
2. customseal tube
3. customReaction completion
4. customThe reaction mixture was quenched into the ice-water NaHCO3 solution (50 mL)
5. extractionwas extracted with ethyl acetate (3×50 mL)
6. washOrganic layer was washed with brine solution (3×50 mL)
7. customThe organic layer was dried
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customto provide the 0.3 g of crude compound
11. customThe compound was purified by column chromatography
12. washCompound was eluted out at 30% ethyl acetate in hexane

ORD record

ord-744e22b2f10c4749b8309de3e000c898

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428490B2