Trifluoroacetic acid → 4-propyl-1-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyrrolidin-2-one
Reaktionsgleichung
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C(O)(C(F)(F)F)=O.O[CH2:18][N:19]1[CH2:23][CH:22]([CH2:24][CH2:25][CH3:26])[CH2:21][C:20]1=[O:27]>>[CH2:24]([CH:22]1[CH2:23][N:19]([CH2:18][C:3]2[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:1][CH:2]=2)[C:20](=[O:27])[CH2:21]1)[CH2:25][CH3:26]Komponenten
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
To a solution of commercially available 1H-pyrrolo[2,3-b]pyridine x7 (20.31 mmol, 1.2 eq, 3.19 g) dissolved TFA (25 ml) is added 1-(hydroxymethyl)-4-propylpyrrolidin-2-one x2 (16.93 mmol, 1 eq, 2 g). The mixture is heated at 70° C. overnight. The solvent is then evaporated under reduce pressure. CH2Cl2 (600 ml) is then added to the residue, and the resulting organic solution is washed with a saturated aqueous solution of sodium carbonate (200 ml). The organic phase is then dried over MgSO4 and the volatiles are removed under reduced pressure. The product is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 97/3/0.3 (v/v/v)) and recristallized in acetonitrile. 4-propyl-1-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyrrolidin-2-one 231 is obtained as a white solid.
Aufarbeitung
- customThe solvent is then evaporated
- additionCH2Cl2 (600 ml) is then added to the residue
- washthe resulting organic solution is washed with a saturated aqueous solution of sodium carbonate (200 ml)
- dry with materialThe organic phase is then dried over MgSO4
- customthe volatiles are removed under reduced pressure
- customThe product is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 97/3/0.3 (v/v/v))
Quellen und Nachweise
- ORD-Eintrag
- ord-63fe9b9371f8428f99f6aaaaf213a3e9
- Quelldatensatz
- uspto-grants-2013_08
- Patentnummer
- US08518943B2
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