Potassium Carbonate → Diethyl 1-(1-cyanoethyl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

HRID 1521718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521718
[NH:1]1[C:5]2=[N:6][C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+].Br[CH:27]([CH3:30])[C:28]#[N:29]>CN(C=O)C>[C:28]([CH:27]([N:1]1[C:5]2=[N:6][C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:30])#[N:29]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 1405382-BromopropionitrileHCID 67236396Diethyl 1H-pyrrolo[2,3-B]pyridine-2,6-dicarboxylate2×

Produkt 1

HCID 67236322Diethyl 1-(1-cyanoethyl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylateAusbeute 43,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of diethyl 1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (Intermediate D, 1.55 g, 5.91 mmol) in DMF (15 mL) is added potassium carbonate (2.45 g, 17.7 mmol), and the mixture is stirred at room temperature for 20 min. 2-bromopropionitrile (1.05 mL, 11.8 mmol) is added, the mixture is warmed to 80° C., and is stirred overnight. After being cooled to room temperature, the mixture is poured onto H2O, and the aqueous layer is extracted with EtOAc (3×100 mL). The combined organic extracts are dried (MgSO4), filtered, and concentrated. The crude material is purified via flash column chromatography using a gradient elution of 10-50% ethyl acetate/hexanes to afford the title compound as a bright yellow solid (809 mg, 43%).

Aufarbeitung

  1. temperaturethe mixture is warmed to 80° C.
  2. stirringis stirred overnight
  3. temperatureAfter being cooled to room temperature
  4. additionthe mixture is poured onto H2O
  5. extractionthe aqueous layer is extracted with EtOAc (3×100 mL)
  6. dry with materialThe combined organic extracts are dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material is purified via flash column chromatography
  10. washa gradient elution of 10-50% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3cf1058b80164a44a93a0dcc074f5606
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073926B2

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