Methyl chloroformate → Ethyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

HRID 857455Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857455
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][N+:8]=2[O-])[CH:3]=[C:2]1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[Cl:16]C(OC)=O>C1COCC1>[Cl:16][C:7]1[N:8]=[C:9]2[C:4]([CH:3]=[C:2]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:1]2)=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 6586Methyl chloroformateHCID 178468513HCID 178468513, Verbindung

Produkt 1

HCID 21868758Ethyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylateAusbeute 26,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of ethyl 7-azaindole-2-carboxylate-7-oxide (1.32 g, 6.4 mmol) and hexamethyldisilazale (1.4 mL, 6.6 mmol) in THF (30 mL) at 0° C. was added dropwise over 30 min a solution of methyl chloroformate (1.2 mL, 15.5 mmol) in THF (5 mL). The mixture was warmed to room temperature, stirred for 2 h and partitioned between ether (50 mL) and water (50 mL). The aqueous layer was extracted with ether (30 mL). The combined organic extracts were washed (water, brine), dried (sodium sulfate) and purified by column chromatography [SiO2; heptane-ether (3:1)] to give ethyl 6-chloro-7-azaindole-2-carboxylate as a white solid (0.38 g, 26%). mp 144–145° C. Found: C, 53.69; H, 4.05; N, 12.39%. C10H9N2ClO2 requires: C, 53.47; H, 4.04; N, 12.46%.

Aufarbeitung

  1. custompartitioned between ether (50 mL) and water (50 mL)
  2. extractionThe aqueous layer was extracted with ether (30 mL)
  3. washThe combined organic extracts were washed (water, brine)
  4. dry with materialdried (sodium sulfate)
  5. custompurified by column chromatography [SiO2; heptane-ether (3:1)]

Quellen und Nachweise

ORD-Eintrag
ord-22f1a90dea4d4b10a3dbc241cfc90e39
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07145009B2

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