Dimethylformamide → (3-Cyano-pyrazolo[3,4-b]pyridin-1-yl)-acetic acid tert-butyl ester

HRID 503881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503881
[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10](I)=[N:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:19][N:20](C=O)C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[C-]#N.[C-]#N.[Zn+2].O>[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([C:19]#[N:20])=[N:9]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 2

HCID 6228DimethylformamideHCID 57978086(3-Iodo-pyrazolo[3,4-b]pyridin-1-yl)-acetic acid tert-butyl ester

Produkt 1

HCID 57978082(3-Cyano-pyrazolo[3,4-b]pyridin-1-yl)-acetic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A 250 mL flask was charged with (3-iodo-pyrazolo[3,4-b]pyridin-1-yl)-acetic acid tert-butyl ester (15.0 g), PdCl2(dppf) (3.0 g), Zn(CN)2 (4.96 g), DMF (200 mL) and H2O (14 mL). The flask containing the resultant suspension was degassed and backfilled with nitrogen gas repeatedly for 5 minutes, followed by addition of Pd2(dba)3 (3.85 g) to the reaction mixture. The reaction mixture was heated under N2 at 90° C. for 16 h, cooled to room temperature, diluted with H2O (800 mL) and filtered. The collected solid was washed with toluene (10 mL) to provide (3-cyano-pyrazolo[3,4-b]pyridin-1-yl)-acetic acid tert-butyl ester as a yellow solid.

Aufarbeitung

  1. customwas degassed
  2. additionfollowed by addition of Pd2(dba)3 (3.85 g) to the reaction mixture
  3. temperaturecooled to room temperature
  4. additiondiluted with H2O (800 mL)
  5. filtrationfiltered
  6. washThe collected solid was washed with toluene (10 mL)

Quellen und Nachweise

ORD-Eintrag
ord-2f25144b922d45e2bf3d664f480569b8
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07777035B2

Notizen zur Reaktion

Wird geladen…