Sodium Azide → HCID 86609940, Verbindung

HRID 503869Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503869
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8](CBr)=[N:7]1)[CH3:2].[N-:18]=[N+:19]=[N-:20].[Na+]>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]([N:18]=[N+:19]=[N-:20])=[N:7]1)[CH3:2]

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 57642772Ethyl [3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl]acetate

Produkt 1

HCID 86609940HCID 86609940, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of (3-(bromomethyl)-pyrazolo[3,4-b]pyridine-1-yl)acetic acid ethyl ester (0.5 Mmol, 1 eq.) and sodium azide (1 Mmol, 2 eq.) in 1 mL of DMF was heated at 80° C. for 1 h. The resultant mixture was cooled to rt, diluted with 150 mL of EtOAc, washed with water (40 mL××3), brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The solvent was removed in vacuo to provide 135.2 Mg desired product: HPLC retention time=1.84 minutes (Agilent Zorbax SB-C18, 2.1×50 Mm, 5μ, 35° C.) using 1 mL/min flow rate, a 2.5 minute gradient of 20% to 100% B with a 1.1 minute wash at 100% B (A=0.1% formic acid/5% acetonitrile/94.9% water, B=0.1% formic acid/5% water/94.9% acetonitrile); MS (ES) M+H expect=261.1, found=261.4.

Aufarbeitung

  1. washwashed with water (40 mL××3), brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9b7c9eb81bb74d86b45b34585cba9e87
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07777035B2

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