Selectfluor → 1-(4-chloro-2-trifluoromethyl-benzyl)-3-fluoro-1H-indazole-5-carbaldehyde

HRID 2400968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2400968
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([CH:16]=[O:17])=[CH:13][CH:14]=3)[CH:9]=[N:8]2)=[C:4]([C:20]([F:23])([F:22])[F:21])[CH:3]=1.[B-](F)(F)(F)[F:25].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CC#N>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([CH:16]=[O:17])=[CH:13][CH:14]=3)[C:9]([F:25])=[N:8]2)=[C:4]([C:20]([F:22])([F:23])[F:21])[CH:3]=1

Komponenten

4

Edukt 2

HCID 2724933SelectfluorHCID 866545471-(4-chloro-2-(trifluoromethyl)benzyl)-1H-indazole-5-carbaldehyde

Produkt 1

HCID 866596991-(4-chloro-2-trifluoromethyl-benzyl)-3-fluoro-1H-indazole-5-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A suspension of 1-[4-Chloro-2-(trifluoromethyl)benzyl]-1H-indazol-5-carbaldehyde (0.9 mmol, from Example 1)) and SelectFluor® (2 eq., Aldrich) in CH3CN (3 mL) was heated in a microwave reactor at 140° C. for 30 min. The solvent was evaporated and the residue was washed with DCM. The insoluble solid was discarded. The combined organic washings were concentrated and the residue was purified by flash chromatography (0-20% EtOAc/Hex) to afford 1-[4-chloro-2-(trifluoromethyl)benzyl]-3-fluoro-1H-indazol-5-carbaldehyde.

Aufarbeitung

  1. customThe solvent was evaporated
  2. washthe residue was washed with DCM
  3. concentrationThe combined organic washings were concentrated
  4. customthe residue was purified by flash chromatography (0-20% EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-c4f14e175b9042ee9f8c66e6293ca043
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08796256B2

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