1,2-Difluoro-4-nitrobenzene → 6-bromo-5-(2-fluoro-4-nitrophenoxy)-1H-indazole

HRID 1661971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1661971
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[OH:11].[F:12][C:13]1[CH:14]=[C:15]([N+:20]([O-:22])=[O:21])[CH:16]=[CH:17][C:18]=1F.C([O-])(O)=O.[Na+].[Li+].[Cl-]>CN(C=O)C.C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[O:11][C:18]1[CH:17]=[CH:16][C:15]([N+:20]([O-:22])=[O:21])=[CH:14][C:13]=1[F:12]

Komponenten

7

Edukt 4

HCID 1230531,2-Difluoro-4-nitrobenzeneHCID 433294Lithium ChlorideHCID 516892Sodium BicarbonateHCID 591599466-Bromo-1H-indazol-5-ol

Produkt 1

HCID 667671536-bromo-5-(2-fluoro-4-nitrophenoxy)-1H-indazoleAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 6-bromo-5-hydroxy-1H-indazole (7.0 g, 33.0 mmol), 3,4-difluoronitrobenzene (4.98 mg, 31.0 mmol), NaHCO3 (2.5 g, 31.0 mmol) in DMF (100 mL) is stirred at 80° C. for 4 hours. Then LiCl (10% aqueous solution) is added and the solution is extracted with EtOAc. The organic phase is dried over anhydrous MgSO4, filtered and concentrated. The residue is purified by silica gel column chromatography eluting with PE:DCM (1:1) to give the desired product (5.5 g, 46.6% yield). MS (m/z): 354.0 (M+H).

Aufarbeitung

  1. extractionthe solution is extracted with EtOAc
  2. dry with materialThe organic phase is dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel column chromatography
  6. washeluting with PE

Quellen und Nachweise

ORD-Eintrag
ord-2834e9e657a443aabaa3f6184b648543
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030302B2

Notizen zur Reaktion

Wird geladen…