Iodine → HCID 86680376, compound

HRID 83543Notes

Reaction equation

HRID 83543 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:12]=[CH:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.C([Li])CCC.[I:25]I.S([O-])([O-])=O.[Na+].[Na+]>O1CCCC1>[CH3:1][C:2]1[N:3]([C:8]2[CH:12]=[C:11]([I:25])[N:10]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 807IodineHCID 24437Sodium SulfiteHCID 712878593-(2,5-dimethylpyrrol-1-yl)-1-(4-fluorophenyl)-1H-pyrazoleHCID 178418339Butyllithium

Product 1

HCID 86680376HCID 86680376, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon atmosphere, a solution of 3-(2,5-dimethylpyrrol-1-yl)-1-(4-fluorophenyl)-1H-pyrazole (599 mg) in tetrahydrofuran (4 ml) was cooled to −78° C., n-butyllithium (1.8 ml, 1.6M solution in n-hexane) was added dropwise thereto, and the mixture was stirred for 30 minutes. To this reaction solution was added dropwise a solution of iodine (715 mg) in tetrahydrofuran (2 ml), the mixture was stirred for additional 30 minutes. To this reaction mixture was added a saturated aqueous solution of sodium sulfite, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. To the resulting solid residue was added a mixed solvent of ethyl acetate/n-hexane (=1/5), and the mixture was stirred. A solid was collected from this suspension by filtration, dried under reduced pressure to give the titled compound (625 mg).

Workup

  1. stirringthe mixture was stirred for additional 30 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe resulting organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the resulting solid residue was added a mixed solvent of ethyl acetate/n-hexane (=1/5)
  7. stirringthe mixture was stirred
  8. filtrationA solid was collected from this suspension by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-f8e6423090ff409f84f810b73177d44e
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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