Ethyl alpha-Azido-beta-(4-methoxypyrid-3-yl)-acrylate → Ethyl 4-methoxy-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

HRID 1445920

Reaktionsgleichung

Reaktionsgleichung von HRID 1445920
[N:1]([C:4](=[CH:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-]>CC1C=CC=CC=1C>[CH2:8]([O:7][C:5]([C:4]1[NH:1][C:12]2=[N:13][CH:14]=[CH:15][C:16]([O:17][CH3:18])=[C:11]2[CH:10]=1)=[O:6])[CH3:9]

Komponenten

3

Edukt 1

HCID 72796408Ethyl alpha-Azido-beta-(4-methoxypyrid-3-yl)-acrylate

Produkt 1

HCID 11736140Ethyl 4-methoxy-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A stirred solution of ethyl-α-azido-β-(4-methoxypyrid-3-yl)-acrylate 2 (3.7 g, 14.9 mmol) in dry o-xylene (35 mL) was heated in an oil bath at 170° C. for 25 min. During this time the contents of the flask gained brick red color. After cooling, the mixture was concentrated under high vacuum. The resultant brown residue was purified on silica gel column using 5% methanol in CH2Cl2 to give 3 as brick red solid. Mp 195-197° C.; Yield: 3.3 g, 82%; ESI MS: m/z 220.9 (M+1).

Aufarbeitung

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated under high vacuum
  3. customThe resultant brown residue was purified on silica gel column
  4. customto give 3 as brick red solid

Quellen und Nachweise

ORD-Eintrag
ord-1feb00a08af34c57a4e5d752862b7d45
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666898B2

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