Methyl iodide → HCID 67363339, Verbindung

HRID 245756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 245756
[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[NH:8][C:5]2=[N:6][CH:7]=1.[C:15](=O)([O-])[O-].[K+].[K+].IC>[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[N:8]([CH3:15])[C:5]2=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 45073274Methyl 5-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Produkt 1

HCID 67363339HCID 67363339, VerbindungAusbeute 84,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 5-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (0.986 g, 4.68 mmol) N,N-dimethylformamide (20 ml) at room temperature under a nitrogen atmosphere was added potassium carbonate (0.647 g, 4.68 mmol). After 30 minutes iodomethane (0.321 ml, 5.15 mmol) was added and the resulting mixture was stirred at room temperature overnight. Brine was added and the mixture was extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was coated onto hydromatrix and purified by column chromatography (silica gel; heptane/ethyl acetate 4/1) to give methyl 5-chloro-1-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (0.89 g).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate three times
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography (silica gel; heptane/ethyl acetate 4/1)

Quellen und Nachweise

ORD-Eintrag
ord-f70d071458a64d8e91ad8f7d10757743
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658794B2

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