Water → HCID 25130781, compound

HRID 2262532Notes

Reaction equation

HRID 2262532 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:8][O:9][C:10]=2[C:11]([F:14])([F:13])[F:12])[N:3]=[CH:2]1.F[C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:15]1([C:7]2[C:6]([C:4]3[N:3]=[CH:2][N:1]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)[CH:5]=3)=[C:10]([C:11]([F:14])([F:12])[F:13])[O:9][N:8]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67873Benzene, 1-fluoro-4-(trifluoromethyl)-HCID 178506308HCID 178506308, compound

Product 1

HCID 25130781HCID 25130781, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-(1H-imidazol-4-yl)-3-phenyl-5-trifluoromethyl-isoxazole (69.8 mg, 0.25 mmol) in DMF (1.0 mL) was added 4-fluorobenzotrifluoride (32 μL, 41 mg, 0.25 mmol) and potassium carbonate (69.1 mg, 0.5 mmol) and the resulting mixture heated at 120° C. overnight. The resulting mixture was then poured into water and extracted with ethyl acetate which was then washed with brine, dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=60:40) afforded the title compound (68 mg, 64%) which was obtained as an off-white solid. MS: m/e=424.3 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate which
  2. washwas then washed with brine
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customPurification by chromatography (SiO2, heptane:ethyl acetate=60:40)

Sources & evidence

ORD record
ord-0731d2463417432aaf629e3e992454d7
Source dataset
uspto-grants-2010_12
Patent number
US07851469B2

Reaction notes

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