Reaktion #62201

Reaktionsgleichung

4-(4-((quinolin-2-yl)methoxy)phenyl)-3-(pyridin-4-yl)but-3-en-2-one

p-toluensulfonylhydrazine

p-toluenesulfonylhydrazine

→

2-((4-(3-Methyl-4-(pyridin-4-yl)-1H-pyrazol-5-yl)phenoxy)methyl)quinoline

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for 10 h
3. 3
   Temperaturthe mixture heated
4. 4
   Temperaturat reflux 2 h
5. 5
   EinengenThe mixture was concentrated
6. 6
   workup.DISSOLUTIONthe residue dissolved in dichloromethane
7. 7
   Waschenthe resulting solution washed with water (2×25 mL)
8. 8
   Sonstigedried
9. 9
   Einengenconcentrated
10. 10
    SonstigeThe residue was chromatographed on silica
11. 11
    Wascheneluted with 1%, 2%, and 3% methanol in dichloromethane containing 0.5% concentrated ammonium hydroxide giving a solid which
12. 12
    Sonstigewas triturated with ether
13. 13
    Sonstigedried
14. 14
    SonstigeHPLC-MS (system 1) 4.65 min, m/e 393 (MH+)

Vorschrift

A mixture of 4-(4-((quinolin-2-yl)methoxy)phenyl)-3-(pyridin-4-yl)but-3-en-2-one (1.00 g, 2.60 mmol) and p-toluensulfonylhydrazine (484 mg, 2.6 mmol) in acetic acid (14 mL) was heated at reflux for 10 h. Additional p-toluenesulfonylhydrazine (242 mg, 0.5 mmol) was added and the mixture heated at reflux 2 h. The mixture was concentrated, the residue dissolved in dichloromethane and the resulting solution washed with water (2×25 mL), dried and concentrated. The residue was chromatographed on silica eluted with 1%, 2%, and 3% methanol in dichloromethane containing 0.5% concentrated ammonium hydroxide giving a solid which was triturated with ether and dried. Yield 293 mg, 29%. 1H NMR (CDCl3, 400 mHz) δ 8.51 (m, 2H), 8.18 (d, 1H, J=8.7 Hz), 8.06 (d, 1H, J=7.9 Hz), 7.81 (d, 1H, J=8.3 Hz), 7.72 (m, 1H), 7.64 (d, 1H, J=8.3 Hz), 7.54 (m, 1H), 7.24 (m, 2H), 7.13 (m, 2H), 6.96 (m, 2H), 5.36 (s, 2H), 2.33 (s, 3H). HPLC-MS (system 1) 4.65 min, m/e 393 (MH+).

Quelle