Water → 6-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-(2-methylallyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1909199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1909199
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([NH:13][CH2:14][C:15]2[C:16](=[O:23])[NH:17][C:18]([CH3:22])=[CH:19][C:20]=2[CH3:21])=[O:12])[C:5]2[CH:10]=[N:9][NH:8][C:6]=2[N:7]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH:31]=[C:32]([CH3:34])[CH3:33].O>CN(C=O)C.CO.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:11]([NH:13][CH2:14][C:15]2[C:16](=[O:23])[NH:17][C:18]([CH3:22])=[CH:19][C:20]=2[CH3:21])=[O:12])[C:5]2[CH:10]=[N:9][N:8]([CH2:33][C:32]([CH3:34])=[CH2:31])[C:6]=2[N:7]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 105551-Propene, 1-chloro-2-methyl-HCID 11430Potassium CarbonateHCID 867034116-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Produkt 1

HCID 867034136-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-(2-methylallyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamideAusbeute 46,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 6-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.4 g, 1.0 mmol) in DMF (4 mL), K2CO3 (0.152 g, 1.10 mmol) and 3 chloro-2-methylpropene (0.115 g, 1.27 mmol) were added. Resulting reaction mixture was stirred at 80° C. for 2 h. On completion of reaction, water was added to it and extraction was carried out using 20% MeOH/DCM; the combined organic layers were washed with water, brine and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure and residue was purified by silica gel column chromatography to obtain the desired intermediate (0.2 g, 43.8%).

Aufarbeitung

  1. customResulting
  2. customreaction mixture
  3. additionwas added to it and extraction
  4. washthe combined organic layers were washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customSolvent was removed under reduced pressure and residue
  7. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c3e5fa69b5e144a988e1a8398d1803fb
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598167B1

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