Iodine → 1-(4-chlorophenyl)-3-(2,5-dimethylpyrrol-1-yl)-5-iodo-1H-pyrazole

HRID 83534Notes

Reaction equation

HRID 83534 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]([Cl: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>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([N:10]2[C:11]([I:25])=[CH:12][C:8]([N:3]3[C:4]([CH3:7])=[CH:5][CH:6]=[C:2]3[CH3:1])=[N:9]2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 807IodineHCID 24437Sodium SulfiteHCID 866803671-(4-Chlorophenyl)-3-(2,5-dimethylpyrrol-1-yl)-1H-pyrazoleHCID 178418339Butyllithium

Product 1

HCID 866803691-(4-chlorophenyl)-3-(2,5-dimethylpyrrol-1-yl)-5-iodo-1H-pyrazoleYield 57.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon atmosphere, a solution of 3-(2,5-dimethylpyrrol-1-yl)-1-(4-chlorophenyl)-1H-pyrazole (4.98 g) in tetrahydrofuran (40 ml) was cooled to −78° C., n-butyllithium (13.7 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 (5.58 g) in tetrahydrofuran (10 ml), the mixture was stirred for 30 minutes. To this reaction solution were added a 20 wt % aqueous solution of sodium sulfite and a saturated aqueous solution of ammonium chloride, the mixture was extracted with ethyl acetate. The 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=1/2, the mixture was stirred. A solid was collected from this suspension by filtration, and was dried under reduced pressure to give the titled compound (4.19 g).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractiona saturated aqueous solution of ammonium chloride, the mixture was extracted with ethyl acetate
  3. washThe 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=1/2
  7. stirringthe mixture was stirred
  8. filtrationA solid was collected from this suspension by filtration
  9. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-351fd4fc5d254c37a84a4ac92d24eb55
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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