Water → 5-(3,5-difluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-amine
Reaktionsgleichung
C(Cl)Cl.[Cl-].[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([F:14])[CH:13]=1)[CH2:9][Zn+].Br[C:16]1[CH:17]=[C:18]2[C:24]([NH2:25])=[N:23][NH:22][C:19]2=[N:20][CH:21]=1.O>O1CCCC1>[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([F:14])[CH:13]=1)[CH2:9][C:16]1[CH:17]=[C:18]2[C:24]([NH2:25])=[N:23][NH:22][C:19]2=[N:20][CH:21]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
CH2Cl2 and 28 ml (14.08 mmol) of 3,5-difluorobenzyl zinc (II) chloride are added to 1.5 g (7.04 mmol) of a solution of 5-bromo-1H-pyrazolo[3,4-b]pyridin-3-amine in 10 ml of tetrahydrofuran. The reaction medium is heated at 90° C. for 18 hours. After returning to room temperature, the reaction is hydrolyzed by slowly adding water at 0° C. After filtration of the precipitate formed, the solid is rinsed with tetrahydrofuran and the aqueous filtrate is extracted several times with ethyl acetate. The organic phases are combined, dried on magnesium sulfate and concentrated. The residue is purified by silica chromatography (95:4.5:0.5 and then 95:4:1 dichloromethane/methanol/ammonium as eluent) to yield 1.7 g (93%) of 5-(3,5-difluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-amine in the form of a beige solid.
Aufarbeitung
- customAfter returning to room temperature
- filtrationAfter filtration of the precipitate
- customformed
- washthe solid is rinsed with tetrahydrofuran
- extractionthe aqueous filtrate is extracted several times with ethyl acetate
- customdried on magnesium sulfate
- concentrationconcentrated
- customThe residue is purified by silica chromatography (95:4.5:0.5
Quellen und Nachweise
- ORD-Eintrag
- ord-3f4fbaa15f3d42db83a991e6f03d9fd1
- Quelldatensatz
- uspto-grants-2016_07
- Patentnummer
- US09381195B2
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