Potassium Carbonate → 6-Methyl-1-phenyl-1H-indazol-4-amine

HRID 551424Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 551424
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[CH:6]=[N:7][NH:8][C:9]=2[CH:10]=1.I[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]I>[CH3:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[CH:6]=[N:7][N:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:9]=2[CH:10]=1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 193544286-Methyl-1H-indazol-4-amine

Produkt 1

HCID 249380596-Methyl-1-phenyl-1H-indazol-4-amineAusbeute 30,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

6-Methyl-1H-indazol-4-amine (75 mg, 0.51 mmol) and iodobenzene (104 mg, 0.51 mmol) were dissolved in DMF (0.55 ml) in a microwave tube. Copper (I) iodide (19 mg, 0.1 mmol), trans-N,N′-dimethyl-1,2-cyclohexanediamine (28.5 mg, 0.2 mmol) and potassium carbonate (140.9 mg, 1.02 mmol) were added and the mixture heated by microwave (250 W) at 100° C. for 20 minutes. The mixture was filtered through a cartridge, washing with DCM (5 ml) and the filtrate was evaporated to dryness and purified by mass-directed autopreparation (system B). The appropriate fractions were combined, extracted with DCM, washed with aqueous sodium bicarbonate, dried through a hydrophobic frit and evaporated to give the title compound (34.9 mg).

Aufarbeitung

  1. filtrationThe mixture was filtered through a cartridge
  2. washwashing with DCM (5 ml)
  3. customthe filtrate was evaporated to dryness
  4. custompurified by mass-directed autopreparation (system B)
  5. extractionextracted with DCM
  6. washwashed with aqueous sodium bicarbonate
  7. customdried through a hydrophobic frit
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-cc05786270a244cca47218eaa486684f
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947727B2

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