Potassium Carbonate → ethyl 2-[2-nitro-4-(trifluoromethyl)phenyl]-5-[3-(trifluoromethoxy)phenoxy]-2H-1,2,3-triazole-4-carboxylate

Temperature

80 °C

To a solution of ethyl 5-[3-(trifluoromethoxy)phenoxy]-2H-1,2,3-triazole-4-carboxylate (i.e. the product of Step E, 0.55 g, 1.7 mmol) in N,N-dimethylformamide (5 mL) was added anhydrous potassium carbonate (0.48 g, 3.5 mmol) and 4-fluoro-3-nitrobenzotrifluoride (0.29 mL, 2.1 mmol). The mixture was heated to 80° C. with stirring for 90 min. The reaction mixture was concentrated to dryness under reduced pressure. The resulting residue was diluted with water (10 mL) and extracted with ethyl acetate (30 mL, 15 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford the crude product. The crude material was purified by chromatography on silica gel eluting with 0 to 20% ethyl acetate in hexanes to obtain the title compound (0.76 g) as a pale yellow oil.

1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
2. additionThe resulting residue was diluted with water (10 mL)
3. extractionextracted with ethyl acetate (30 mL, 15 mL)
4. dry with materialThe organic layer was dried (MgSO4)
5. concentrationconcentrated under reduced pressure
6. customto afford the crude product
7. customThe crude material was purified by chromatography on silica gel eluting with 0 to 20% ethyl acetate in hexanes

ORD record

ord-ae90cb27957c40c3aec800f64334b190

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09302999B2