N-Iodosuccinimide → 3-bromo-5-(2-chloro-4-fluorophenyl)-4-iodo-1-methyl-1H-pyrazole

HRID 406595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 406595
[Br:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=2[Cl:14])[N:4]([CH3:15])[N:3]=1.[I:16]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[C:6]([I:16])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=2[Cl:14])[N:4]([CH3:15])[N:3]=1

Komponenten

5

Edukt 2

HCID 120273N-IodosuccinimideHCID 666135773-bromo-5-(2-chloro-4-fluorophenyl)-1-methyl-1H-pyrazole2×

Produkt 1

HCID 666138253-bromo-5-(2-chloro-4-fluorophenyl)-4-iodo-1-methyl-1H-pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a mixture of 3-bromo-5-(2-chloro-4-fluorophenyl)-1-methyl-1H-pyrazole (i.e. the product of Step C) (620 mg, 2.14 mmol) in N,N-dimethylformamide (8 mL) at 60° C. was added N-iodosuccinimide (963 mg, 4.28 mmol). The reaction mixture was stirred at 60° C. for 3 h, and then diluted with ethyl acetate, washed with water and saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The material was purified by silica gel chromatography (5 to 30% gradient of ethyl acetate in hexanes as eluant) to provide the title compound as a pale yellow solid (515 mg) melting at 139-141° C.

Aufarbeitung

  1. washwashed with water and saturated aqueous sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe material was purified by silica gel chromatography (5 to 30% gradient of ethyl acetate in hexanes as eluant)

Quellen und Nachweise

ORD-Eintrag
ord-e4b763cf75694b3f803eada609ef983d
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754115B2

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