Iodine → HCID 67384758, compound

HRID 1471914Notes

Reaction equation

HRID 1471914 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:5]=2)[CH2:3][CH2:2]1.[I-:15].[Na+].II.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5]=2[I:15])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 807IodineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 67384503HCID 67384503, compound

Product 1

HCID 67384758HCID 67384758, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-cyclopropyl-3-phenyl-1H-pyrazole (3.0 g, 16.28 mmol) in THF (20 mL) and water (20 mL) were added sodium iodide (2.441 g, 16.28 mmol), iodine (6.20 g, 24.43 mmol), and potassium carbonate (3.38 g, 24.43 mmol) at room temperature. The reaction was brought to reflux for 2 h at 100° C. The reaction was cooled to room temperature and quenched with 10% aq. Na2SO3. The organic solvent was removed under reduced pressure and the aqueous was extracted with EtOAc, washed with NaHCO3 solution, brine, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography to give the title compound (2.7 g). LCMS m/z=310.8 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.75-0.81 (m, 2H), 0.83-0.88 (m, 2H), 2.46-2.56 (m, 1H), 7.33-7.47 (m, 3H), 7.62-7.71 (m, 2H), 12.91 (s, 1H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customquenched with 10% aq. Na2SO3
  3. customThe organic solvent was removed under reduced pressure
  4. extractionthe aqueous was extracted with EtOAc
  5. washwashed with NaHCO3 solution, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-661548a524ae4556b3e1e61693462098
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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