4-Chloroaniline → 1-(4-Chlorophenylamino)-4-(4-pyridylmethoxy)pyridazine

Temperatur

80 °C

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.

1. temperatureupon heating
2. temperatureThe mixture was cooled to RT
3. washwashed by brine
4. dry with materialthe organic layer was dried over Na2SO4
5. customthe solvent was evaporated in vacuo
6. customThe crude mixture was purified by preparative thin layer plate

ORD-Eintrag

ord-ce55ff32496e413aa622f1323061cad3

Quelldatensatz

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06903101B1