Ammonia → 3-(2,5-dimethylpyrrol-1-yl)-1-(3-fluorophenyl)-5-iodo-1H-pyrazole

HRID 83498

Reaktionsgleichung

Reaktionsgleichung von HRID 83498
[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]=[C:15]([F:19])[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)=S.[Na+].[Na+].N>O1CCCC1>[CH3:7][C:4]1[N:3]([C:8]2[CH:12]=[C:11]([I:25])[N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Komponenten

7

Edukt 5

HCID 222AmmoniaHCID 807IodineHCID 24477Sodium ThiosulfateHCID 712877533-(2,5-Dimethylpyrrol-1-yl)-1-(3-fluorophenyl)-1H-pyrazoleHCID 178418339Butyllithium

Produkt 1

HCID 866803553-(2,5-dimethylpyrrol-1-yl)-1-(3-fluorophenyl)-5-iodo-1H-pyrazoleAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 3-(2,5-dimethylpyrrol-1-yl)-1-(3-fluorophenyl)-1H-pyrazole (10.4 g) in tetrahydrofuran (100 ml) cooled to −78° C. was added n-butyllithium (1.6M solution in n-hexane, 31 ml) over 10 minutes, and then the mixture was stirred for 30 minutes. To the mixture was added dropwise a solution of iodine (12.4 g) in tetrahydrofuran (20 ml) over 10 minutes, and the mixture was stirred for additional 30 minutes. To the mixture were sequentially added a 20 wt % aqueous solution of sodium thiosulfate and a saturated aqueous ammonia, and then the mixture was warmed to room temperature, and extracted with ethyl acetate. The separated organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To the resulting residue was added a mixed solvent of n-hexane/ethyl acetate (2/1), and the mixture was stirred. The insoluble substance was collected by filtration, and dried under reduced pressure to give the titled compound (4.5 g).

Aufarbeitung

  1. stirringthe mixture was stirred for additional 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe separated 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 residue was added a mixed solvent of n-hexane/ethyl acetate (2/1)
  7. stirringthe mixture was stirred
  8. filtrationThe insoluble substance was collected by filtration
  9. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3204507877d74542bdfba0b2d58ea515
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846746B2

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