Iodine → HCID 67384758, compound

HRID 1471871Notes

Reaction equation

HRID 1471871 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, compound

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 refluxed for 2 h (100° C.). The reaction was cooled to room temperature and quenched with 10% aqueous Na2SO3. The organic solvent was removed under reduced pressure and the aqueous phase was extracted with EtOAc, washed with NaHCO3 solution, brine, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography (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% aqueous Na2SO3
  3. customThe organic solvent was removed under reduced pressure
  4. extractionthe aqueous phase 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 (2.7 g)

Sources & evidence

ORD record
ord-5bfcdf6c27b049818a6602b06352c3a2
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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