1-(Hydroxymethyl)-4-propylpyrrolidin-2-one → 1-[(5-bromo-2H-pyrazolo[3,4-b]pyridin-2-yl)methyl]-4-propylpyrrolidin-2-one

HRID 1896385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1896385
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.O[CH2:12][N:13]1[CH2:17][CH:16]([CH2:18][CH2:19][CH3:20])[CH2:15][C:14]1=[O:21]>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:7]=[N:6][C:5]2=[N:8][N:9]([CH2:12][N:13]3[CH2:17][CH:16]([CH2:18][CH2:19][CH3:20])[CH2:15][C:14]3=[O:21])[CH:10]=[C:4]2[CH:3]=1

Komponenten

4

Edukt 2

HCID 113326021-(Hydroxymethyl)-4-propylpyrrolidin-2-oneHCID 404274545-Bromopyrazolo[3,4-b]pyridine

Produkt 1

HCID 577430451-[(5-bromo-2H-pyrazolo[3,4-b]pyridin-2-yl)methyl]-4-propylpyrrolidin-2-oneAusbeute 7,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of 5-bromo-1H-pyrazolo[3,4-b]pyridine x80 (1 g, 1 eq, 5.04 mmol) and 1-(hydroxymethyl)-4-propylpyrrolidin-2-one x2 (1.58 g, 2 eq, 10.08 mmol) in trifluoroacetic acid (20 ml) is refluxed for 4 hours. The reaction mixture is poured on crushed ice, on saturated NaHCO3 aqueous solution, and the aqueous phase is extracted with dichloromethane. The cumulated organic layers are dried over MgSO4, filtered, evaporated under reduced pressure. The crude product is purified by preparative chromatography on silicagel affording 1-[(5-bromo-2H-pyrazolo[3,4-b]pyridin-2-yl)methyl]-4-propylpyrrolidin-2-one 291 as a white solid.

Aufarbeitung

  1. additionThe reaction mixture is poured
  2. customon crushed ice
  3. extractionon saturated NaHCO3 aqueous solution, and the aqueous phase is extracted with dichloromethane
  4. dry with materialThe cumulated organic layers are dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude product is purified by preparative chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9fefec08376b4a2d80b75b37232e0864
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518943B2

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