Potassium Carbonate → 1-Methyl-1H-pyrazolo[4,3-b]pyridine

HRID 2205287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2205287
Br[C:2]1[C:3]([CH:8]=[N:9][NH:10][CH3:11])=[N:4][CH:5]=[CH:6][CH:7]=1.CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.[Cl-].[NH4+].C(OCC)(=O)C.[Cu]I>[CH3:11][N:10]1[C:2]2[C:3](=[N:4][CH:5]=[CH:6][CH:7]=2)[CH:8]=[N:9]1

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 117696427HCID 117696427, Verbindung

Produkt 1

HCID 569722961-Methyl-1H-pyrazolo[4,3-b]pyridineAusbeute 16,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

N-[1-(3-Bromo-pyridin-2-yl)-methylidene]-N′-methyl-hydrazine (5.7 g, 26.63 mmol), copper (I) iodide (507 mg, 2.66 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (76 mg, 0.533 mmol) and potassium carbonate (7.36 g, 53.25 mmol) are suspended in 1-methyl-2-pyrrolidinone (20 mL) and heated at 120° C. for 3 h. The mixture is diluted with saturated ammonium chloride solution and ethyl acetate. The resulting emulsion is filtered, the phases separated and the organic phase washed with brine, dried and volatiles evaporated under reduced pressure. The residue is redissolved in ethyl ether, washed with brine and the solvent removed. The residue is purified by flash chromatography (0-60% EtOAc in cyclohexane) to give 1-methyl-1H-pyrazolo[4,3-b]pyridine (580 mg, content 85%, 14%)

Aufarbeitung

  1. filtrationThe resulting emulsion is filtered
  2. customthe phases separated
  3. washthe organic phase washed with brine
  4. customdried
  5. customvolatiles evaporated under reduced pressure
  6. dissolutionThe residue is redissolved in ethyl ether
  7. washwashed with brine
  8. customthe solvent removed
  9. customThe residue is purified by flash chromatography (0-60% EtOAc in cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-4ddd3f5ba1bf422c8de5cf9678ef3579
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09371282B2

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