Iodine → HCID 178452207, Verbindung

HRID 387526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387526
[CH:1]1([C:4]2[C:5]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)=[C:6]3[CH:12]=[N:11][NH:10][C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[OH-].[K+].[I:28]I>CN(C=O)C.CCOC(C)=O>[CH:1]1([C:4]2[C:5]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)=[C:6]3[C:12]([I:28])=[N:11][NH:10][C:7]3=[N:8][CH:9]=2)[CH2:2][CH2:3]1

Komponenten

6

Edukt 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 68757650tert-butyl 4-(5-cyclopropyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Produkt 1

HCID 178452207HCID 178452207, VerbindungAusbeute 102 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of tert-butyl 4-(5-cyclopropyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (1.44 g, 4.2 mmol) and powdered potassium hydroxide (692 mg, 10.5 mmol) in DMF (20 mL) was treated with iodine (2.13 g, 8.39 mmol), and the mixture was heated at 60° C. for 5 hours. The mixture was cooled to room temperature, diluted with EtOAc (200 mL) and successively washed with a saturated Na2S2O3 solution (2×20 mL) and water (2×50 mL). The organic layer was separated, dried (MgSO4), filtered, and concentrated in vacuo to provide the crude tert-butyl 4-(5-cyclopropyl-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (2 g, 102% yield) as a solid. LCMS (APCI+) m/z 470.1 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. washsuccessively washed with a saturated Na2S2O3 solution (2×20 mL) and water (2×50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2aecb8bc41f04cd1a7cba7483737720b
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372842B2

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