Methyl iodide → 3-Iodo-1-methyl-1H-pyrazolo[3,4-B]pyridine

HRID 246565Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246565
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.[CH3:11]C(C)([O-])C.[K+].IC>C1COCC1.O>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH3:11])[N:3]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 178506575HCID 178506575, Verbindung

Produkt 1

HCID 534706403-Iodo-1-methyl-1H-pyrazolo[3,4-B]pyridineAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 3-iodo-1H-pyrazolo[3,4-b]pyridine (3.5 g, 14.3 mmol) in THF (70 mL) at 0° C. was added potassium tert-butoxide (1.92 g, 17.1 mmol) and the reaction mixture stirred at 0° C. for 1 h. Iodomethane (2.43 g, 1.07 mL, 17.1 mmol) was added drop-wise, then the mixture was warmed to rt. After 6 h the mixture was diluted with water, extracted with dichloromethane, then the combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. Purification by chromatography (silica, 20-60% ethyl acetate in hexanes) gave 3-iodo-1-methyl-1H-pyrazolo[3,4-b]pyridine (1.14 g, 4.4 mmol, 31%) as an off-white solid. MS (M+H)+=260.

Aufarbeitung

  1. temperaturethe mixture was warmed to rt
  2. extractionextracted with dichloromethane
  3. dry with materialthe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography (silica, 20-60% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-750f9ba1df90465aaebfddd99af7669b
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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