4-Fluoroiodobenzene → 6-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid methyl ester

HRID 1677705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1677705
[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[N:8][NH:9][C:10]=2[CH:11]=[C:12]([Br:14])[CH:13]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[F:21][C:22]1[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=1.CN[C@@H]1CCCC[C@H]1NC>O.C(OCC)(=O)C.[Cu]I.CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[N:8][N:9]([C:25]3[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=3)[C:10]=2[CH:11]=[C:12]([Br:14])[CH:13]=1)=[O:4]

Komponenten

9

Edukt 4

HCID 96054-FluoroiodobenzeneHCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 24728062methyl 6-bromo-1H-indazole-4-carboxylate

Produkt 1

HCID 581387736-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 6-bromo-4-indazolecarboxylic acid methyl ester (2.0 g, 7.8 mmol), copper(I) iodide (0.4 g, 0.2 mmol), potassium carbonate (1.2 g, 8.5 mmol) and 4-fluoroiodobenzene (1.8 g, 8.5 mmol) was charged in a sealed tube at room temperature. The tube was evacuated and back-filled with argon, and DMF (10 mL) and rac-trans-N,N′-dimethylcyclohexane-1,2-diamine (0.20 g, 1.4 mmol) was added. The solution was stirred at 120° C. for 3 hours, cooled to room temperature, and diluted with water (30 mL) and ethyl acetate (50 mL). The organic layer was separated, washed with brine (10 mL) and dried over sodium sulfate. The solvent was removed in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of 0-30% ethyl acetate in hexanes to afford 6-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid methyl ester.

Aufarbeitung

  1. additionwas charged in a sealed tube at room temperature
  2. customThe tube was evacuated
  3. additionwas added
  4. temperaturecooled to room temperature
  5. customThe organic layer was separated
  6. washwashed with brine (10 mL)
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed in vacuo
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with a gradient of 0-30% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8ca364cebcb24a77a6a290ce4b5477df
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008327B2

Notizen zur Reaktion

Wird geladen…