Reaktion #86382

Reaktionsgleichung

4-(6-chloro-2-methylpyridin-3-yl)-6-(trifluoromethyl)-1H-indazole

dicyanozinc

→

title compound

Ausbeute 34.0%

6-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinonitrile

Ausbeute 34.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas thoroughly degassed by nitrogen
2. 2
   TemperaturThe reaction mixture was subsequently cooled
3. 3
   workup.ADDITIONdiluted with EtOAc
4. 4
   Waschenthen washed with brine
5. 5
   TrocknenThe organic layer was dried over Na2SO4
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe residue was purified by CombiFlash® chromatography
8. 8
   Wascheneluting with a gradient of 0-100% EtOAc in hexane
9. 9
   Einengenconcentrated in vacuo

Vorschrift

A mixture of 4-(6-chloro-2-methylpyridin-3-yl)-6-(trifluoromethyl)-1H-indazole (0.97 g, 3.11 mmol), dicyanozinc (1.462 g, 12.45 mmol), and tetrakis(triphenylphoshine)palladium(0) (0.360 g, 0.311 mmol) in DMF (15 mL) was thoroughly degassed by nitrogen and stirred at 120° C. for 24 hours. The reaction mixture was subsequently cooled and diluted with EtOAc then washed with brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by CombiFlash® chromatography, eluting with a gradient of 0-100% EtOAc in hexane. The product-containing fractions were combined and concentrated in vacuo to give the title compound as a white solid (0.32 g, 34%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.39 (s, 3H), 7.45 (d, J=1.01 Hz, 1H), 7.90-8.16 (m, 4H), 13.81 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C15H9F3N4, 303.1. found 303.18.

Quelle