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

HRID 83489Notes

Reaction equation

HRID 83489 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][CH:16]=[CH:15][CH:14]=3)[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.C([Li])CCC.[I:24]I.S([O-])(O)=O.[Na+]>O1CCCC1.O>[CH3:7][C:4]1[N:3]([C:8]2[CH:12]=[C:11]([I:24])[N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 807IodineHCID 23665763Sodium BisulfiteHCID 712878563-(2,5-Dimethylpyrrol-1-yl)-1-phenyl-1H-pyrazoleHCID 178418339Butyllithium

Product 1

HCID 866803513-(2,5-dimethylpyrrol-1-yl)-5-iodo-1-phenyl-1H-pyrazoleYield 58.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(2,5-dimethylpyrrol-1-yl)-1-phenyl-1H-pyrazole (14.6 g) in tetrahydrofuran (80 ml) cooled to −78° C. was added n-butyllithium (1.6M solution in n-hexane, 24 ml) over 5 minutes, and then the mixture was stirred for 1 hour. To this mixture was added a solution of iodine (15.7 g) in tetrahydrofuran (30 ml) over 10 minutes, and the mixture was stirred for additional 1.5 hours. To this mixture were sequentially added water (5 ml) and a saturated aqueous solution of sodium hydrogen sulfite (30 ml), and then the mixture was warmed to 0° C., and additional water (150 ml) was added thereto, and the mixture was stirred at room temperature for 1 hour. A precipitated solid was collected by filtration, washed with water and a small amount of methanol, and dried under reduced pressure to give the titled compound (13.0 g).

Workup

  1. stirringthe mixture was stirred for additional 1.5 hours
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. filtrationA precipitated solid was collected by filtration
  4. washwashed with water
  5. dry with materiala small amount of methanol, and dried under reduced pressure

Sources & evidence

ORD record
ord-bec92af3cad5469eacdf46a5dec791a5
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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