Iodine → HCID 67384889, compound

HRID 1471869Notes

Reaction equation

HRID 1471869 reaction equation
[CH:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=1)([CH3:3])[CH3:2].[I-:15].[Na+].II.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[I:15][C:5]1[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:7][NH:8][C:4]=1[CH:1]([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 807IodineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 15880897HCID 15880897, compound

Product 1

HCID 67384889HCID 67384889, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-isopropyl-3-phenyl-1H-pyrazole (0.64 g, 3.44 mmol) in THF (20 mL) and water (20.00 mL) were added sodium iodide (0.515 g, 3.44 mmol), iodine (1.308 g, 5.15 mmol), and potassium carbonate (0.712 g, 5.15 mmol) at room temperature. The reaction was refluxed for 2 h, cooled to room temperature and quenched with 10% aqueous Na2SO3. The organic solvent was removed under reduced pressure and the aqueous residue was extracted with EtOAc. The organic extract was washed with NaHCO3 solution, brine, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a clear liquid (0.42 g). LCMS m/z=313.2 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.17 (d, J=7.07 Hz, 6H), 3.02 (septet, J=7.07 Hz, 1H), 7.23-7.32 (m, 3H), 7.60-7.67 (m, 2H), 11.81 (bs, 1H).

Workup

  1. temperatureThe reaction was refluxed for 2 h
  2. customquenched with 10% aqueous Na2SO3
  3. customThe organic solvent was removed under reduced pressure
  4. extractionthe aqueous residue was extracted with EtOAc
  5. extractionThe organic extract
  6. washwas washed with NaHCO3 solution, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7109a372e0b147a9869caf8439989f45
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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