Pyrazole → 2-Amino-6-(1H-pyrazol-1-yl)pyridine

HRID 1396444

Reaktionsgleichung

Reaktionsgleichung von HRID 1396444
C([N:8](C(OC(C)(C)C)=O)[C:9]1[N:14]=[C:13](Br)[CH:12]=[CH:11][CH:10]=1)(OC(C)(C)C)=O.[OH-].[K+].[NH:25]1[CH:29]=[CH:28][CH:27]=[N:26]1>CCOC(C)=O.[Cu]>[N:25]1([C:13]2[N:14]=[C:9]([NH2:8])[CH:10]=[CH:11][CH:12]=2)[CH:29]=[CH:28][CH:27]=[N:26]1

Komponenten

6

Edukt 3

HCID 1048PyrazoleHCID 14797Potassium HydroxideHCID 162179716-(Di-Boc-amino)-2-bromopyridine

Produkt 1

HCID 665204692-Amino-6-(1H-pyrazol-1-yl)pyridineAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

6-(Di-Boc-amino)-2-bromopyridine (1.0 g, 2.68 mmol, ChronTech), copper (341 mg, 5.36 mmol), potassium hydroxide (301 mg, 5.36 mmol), and 1H-pyrazole (1.82 g, 26.8 mmol, Eq: 10) were combined and stirred at 160° C. for 18 h. The reaction mixture was cooled, diluted with EtOAc (50 mL) and the solids removed by filtration. The dark blue filtrate was washed with saturated aqueous NaHCO3 and brine then concentrated onto silica gel and purified by chromatography (40 g RediSep column, 20 to 100% ethyl acetate in hexanes, 20 min) to give 6-(1H-pyrazol-1-yl)pyridin-2-amine (365 mg, 2.28 mmol, 85%) as a white solid. MS (EI/CI) m/z: 161.2 [M+H].

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customthe solids removed by filtration
  3. washThe dark blue filtrate was washed with saturated aqueous NaHCO3 and brine
  4. concentrationthen concentrated onto silica gel
  5. custompurified by chromatography (40 g RediSep column, 20 to 100% ethyl acetate in hexanes, 20 min)

Quellen und Nachweise

ORD-Eintrag
ord-a3cd4cc96feb4bd681392ab239d08faa
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901124B2

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