Iodine → HCID 67384889, compound

HRID 1471912Notes

Reaction equation

HRID 1471912 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% aq. 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% aq. 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-0fc10a171f8b44c1b72e18fb1620240a
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

Loading…