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

HRID 623700Notes

Reaction equation

HRID 623700 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[O:7][C:8]1[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:10][NH:11][N:12]=1.C(=O)([O-])[O-].[K+].[K+].F[C:30]1[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][C:31]=1[N+:40]([O-:42])=[O:41]>CN(C)C=O>[N+:40]([C:31]1[CH:32]=[C:33]([C:36]([F:37])([F:38])[F:39])[CH:34]=[CH:35][C:30]=1[N:11]1[N:10]=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:7][C:6]2[CH:18]=[CH:19][CH:20]=[C:4]([O:3][C:2]([F:1])([F:21])[F:22])[CH:5]=2)=[N:12]1)([O-:42])=[O:41]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 178470504HCID 178470504, compound2×

Product 1

HCID 90109335ethyl 2-[2-nitro-4-(trifluoromethyl)phenyl]-5-[3-(trifluoromethoxy)phenoxy]-2H-1,2,3-triazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ae90cb27957c40c3aec800f64334b190
Source dataset
uspto-grants-2016_04
Patent number
US09302999B2

Reaction notes

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