Sodium Cyanide → 6-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrile

HRID 1037560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1037560
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:6]=2Cl.[C-:19]#[N:20].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:6]=2[C:19]#[N:20]

Komponenten

4

Edukt 2

HCID 8929Sodium CyanideHCID 677760136-bromo-3-chloro-2-(4-fluorophenyl)-2H-indazole

Produkt 1

HCID 675136096-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrileAusbeute 54,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a stirred solution of compound (xiii) (4.49 g, 12.86 mmol) in DMF (50 mL) was added sodium cyanide (1.34 g, 27.73 mmol) at RT and the reaction mixture was then heated at 130° C. for 2 h. The reaction mixture was then diluted with saturated FeCl3 solution and extracted with EtOAc (3×75 mL). The combined organic layers were washed with water, dried (Na2SO4) and concentrated to give the crude product which was purified by column chromatography on 100-200 mesh silica gel eluting with EtOAc/hexane (2-4%) to give 6-bromo-2-(4-fluorophenyl)-2H-indazole-3-carbonitrile (xiv) (2.2 g, 50%) as white solid. ESI-MS m/z calculated for [M+H]+: 317.99; found: 317.90.

Aufarbeitung

  1. extractionextracted with EtOAc (3×75 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give the crude product which
  6. customwas purified by column chromatography on 100-200 mesh silica gel eluting with EtOAc/hexane (2-4%)

Quellen und Nachweise

ORD-Eintrag
ord-523d92fec85e47b1901a491436473d00
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546389B2

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