Reaktion #314962

Reaktionsgleichung

2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl

4-(2-(4-aminophenoxy)pyridin-3-yl)-N-methylpyridin-2-amine

1-chloro-4-phenyl-6,7-dihydro-5H-cyclopenta[d]pyridazine

sodium tert-butoxide

→

N-(4-(3-(2-(methylamino)pyridin-4-yl)pyridin-2-yloxy)phenyl)-4-phenyl-6,7-dihydro-5H-cyclopenta[d]pyridazin-1-amine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThis mixture was purged with nitrogen for several minutes
2. 2
   workup.ADDITIONfollowed by addition of 0.780 mL of toluene
3. 3
   SonstigeThe vial was capped
4. 4
   TemperaturUpon cooling
5. 5
   workup.ADDITIONethyl acetate was added
6. 6
   Sonstigea precipitate formed
7. 7
   FiltrationAfter filtration
8. 8
   Waschenwashing with EtOAc
9. 9
   Sonstigethe crude material was purified by ISCO silica gel chromatography (90/10/1 DCM/MeOH/NH4OH, 12 g column)

Vorschrift

A resealable reaction tube was charged with tris(dibenzylideneacetone)dipalladium (0) (0.012 g, 0.013 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (0.021 g, 0.051 mmol), 4-(2-(4-aminophenoxy)pyridin-3-yl)-N-methylpyridin-2-amine (0.075 g, 0.257 mmol), 1-chloro-4-phenyl-6,7-dihydro-5H-cyclopenta[d]pyridazine (0.059 g, 0.257 mmol), and sodium tert-butoxide (0.035 g, 0.359 mmol). This mixture was purged with nitrogen for several minutes, followed by addition of 0.780 mL of toluene. The vial was capped and heated at 100° C. for 1.5 h. Upon cooling, ethyl acetate was added and a precipitate formed. After filtration and washing with EtOAc, the crude material was purified by ISCO silica gel chromatography (90/10/1 DCM/MeOH/NH4OH, 12 g column), to provide N-(4-(3-(2-(methylamino)pyridin-4-yl)pyridin-2-yloxy)phenyl)-4-phenyl-6,7-dihydro-5H-cyclopenta[d]pyridazin-1-amine as a tan solid. MS m/z=487 [M+H]+. Calc'd for C30H26N6O: 486.57.

Quelle