Iodine → HCID 67384704, compound

HRID 1471916Notes

Reaction equation

HRID 1471916 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-:16].[Na+].II.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[I:16][C:11]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][NH:9][C:10]=1[C:12]([F:14])([F:15])[F:13]

Participants

7

Reactant 4

HCID 807IodineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 6113223-Phenyl-5-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 67384704HCID 67384704, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-phenyl-5-(trifluoromethyl)-1H-pyrazole (4.0 g, 18.85 mmol) in THF (50 mL) and water (50 mL) were added sodium iodide (2.83 g, 18.85 mmol), iodine (7.18 g, 28.3 mmol), and K2CO3 (2.61 g, 18.85 mmol) at room temperature. The reaction was refluxed for 16 h, quenched with sodium thiosulfite (2.0 M aq. 10 mL) and concentrated under reduced pressure. The reaction was extracted with ethyl acetate and washed with NaHCO3, brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as white solid (4.0 g). LCMS m/z=338.8 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.39-7.62 (m, 3H), 7.70-7.75 (m, 1H), 7.82-7.88 (m, 1H), 14.11 (s, 1H).

Workup

  1. temperatureThe reaction was refluxed for 16 h
  2. customquenched with sodium thiosulfite (2.0 M aq. 10 mL)
  3. concentrationconcentrated under reduced pressure
  4. extractionThe reaction was extracted with ethyl acetate
  5. washwashed with NaHCO3, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-63c72007ff7849799e539689479ef17b
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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