1-(4-fluorophenyl)-1H-indazole-5-carbaldehyde → 1-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutan-1-ol

HRID 563411

Reaktionsgleichung

Reaktionsgleichung von HRID 563411
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]=[O:18])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH2:19]([Mg]Br)[CH:20]([CH3:22])[CH3:21]>C1COCC1.CCOCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([OH:18])[CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 579436121-(4-fluorophenyl)-1H-indazole-5-carbaldehydeHCID 178418816HCID 178418816, Verbindung

Produkt 1

HCID 670061961-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutan-1-olAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To solution of 1-(4-fluorophenyl)-1H-indazol-5-carboxaldehyde (1.0 g, 4.1 mmol) in 10 mL of THF was added 2.0 M isobutylmagnesium bromide in ether. The reaction mixture was stirred 2 h and then quenched with MeOH. Poured into sat. KH2PO4 and extracted with EtOAc×3. The organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by SiO2 chromatography eluting with 5% EtOAc/DCM. Obtained 650 mg (49% yield) of 1-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutan-1-ol. MS found: (M+H)+=299.

Aufarbeitung

  1. customquenched with MeOH
  2. additionPoured into sat. KH2PO4
  3. extractionextracted with EtOAc×3
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by SiO2 chromatography
  8. washeluting with 5% EtOAc/DCM

Quellen und Nachweise

ORD-Eintrag
ord-07861051b2b44dcc80136865bcd75bab
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067447B2

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