Reaktion #1157718

Reaktionsgleichung

1-bromo-4-(4-pyridylmethoxy)pyridazine

4-chloroaniline

sodium t-butyloxide

→

title compound

Ausbeute 10.0%

1-(4-chlorophenylamino)-4-(4-pyridylmethoxy)pyridazine

Ausbeute 10.0%

Lösungsmittel

ethyl acetate

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturupon heating
2. 2
   TemperaturThe mixture was cooled to RT
3. 3
   Waschenwashed by brine
4. 4
   Trocknenthe organic layer was dried over Na2SO4
5. 5
   Sonstigethe solvent was evaporated in vacuo
6. 6
   SonstigeThe crude mixture was purified by preparative thin layer plate

Vorschrift

To 1-bromo-4-(4-pyridylmethoxy)pyridazine (50 mg, 0.19 mmol) in toluene (3 mL) was added 4-chloroaniline (29 mg, 0.22 mmol), catalytical amount of (R)-(+)2,2′-bis(diphenyl phosphino)-1,1′-binaphthyl (1 mg), tris(dibenzylideneacetone)-dipalladium(0) (0.6 mg) and sodium t-butyloxide (26 mg, 0.27 mmol). The reaction mixture was heated at 80° C. for 12 h under argon. The reaction mixture became deep brown upon heating. The mixture was cooled to RT, diluted with ethyl acetate (10 mL), washed by brine and the organic layer was dried over Na2SO4, and the solvent was evaporated in vacuo. The crude mixture was purified by preparative thin layer plate to afford the title compound (6 mg, yield 10%). 1H-NMR (MeOH-4), 8.51 (d, 2H), 7.61(d, 2H) 7.52(dd, 2H), 7.15-7.25(m, 4H), 5.49(s, 2H); MS ES 313 (M+H)+, 315 (M+3H)+, 316 (M+4H)+, calc. 312; TLC (5:95 v/v methanol-methylene chloride) Rf=0.2.

Quelle