Pyridine → 3-[3-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1,2,4-oxadiazol-5-yl]benzonitrile

HRID 1426546

Reaktionsgleichung

Reaktionsgleichung von HRID 1426546
[OH:1][NH:2][C:3]([C:5]1[C:6]2[CH:13]=[CH:12][N:11]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:7]=2[N:8]=[CH:9][CH:10]=1)=[NH:4].N1C=CC=CC=1.[C:28]([C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33](Cl)=O)#[N:29]>C(#N)C>[CH3:19][Si:18]([CH3:21])([CH3:20])[CH2:17][CH2:16][O:15][CH2:14][N:11]1[C:7]2=[N:8][CH:9]=[CH:10][C:5]([C:3]3[N:4]=[C:33]([C:32]4[CH:31]=[C:30]([CH:38]=[CH:37][CH:36]=4)[C:28]#[N:29])[O:1][N:2]=3)=[C:6]2[CH:13]=[CH:12]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 3084833-Cyanobenzoyl chlorideHCID 178504228HCID 178504228, Verbindung

Produkt 1

HCID 574776613-[3-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1,2,4-oxadiazol-5-yl]benzonitrileAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The crude product N-hydroxy-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine-4-carboximidamide (0.06 gm, 0.0002 mol) was dissolved in pyridine (1.0 mL, 0.012 mol) and then 3-cyanobenzoyl chloride (0.040 g, 0.00024 mol) was added at rt. This mixture was stirred for 1 h and heated to 80° C. in an oil bath. After heating for 18 h the reaction was allowed to cool to rt and then diluted with ACN and concentrated in vacuo to give 3-[3-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1,2,4-oxadiazol-5-yl]benzonitrile 0.08 gm as an off white residue, LC/M S (M+H)+ 418.

Aufarbeitung

  1. temperatureAfter heating for 18 h the reaction
  2. temperatureto cool to rt
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fd9abfb2476b4630a82ad0ba9fd15004
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933086B2

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