Reaktion #453017

Reaktionsgleichung

5-bromo-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine

4-vinylpyridine

tri-o-tolylphosphine

→

title compound

Ausbeute 69.0%

5-(2-(4-Pyridinyl)ethenyl)-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine

Ausbeute 69.0%

Lösungsmittel

acetonitrile

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturat reflux for 16 hours
3. 3
   SonstigeThe solvent was removed
4. 4
   Waschenthe residue was washed with saturated sodium bicarbonate
5. 5
   workup.ADDITIONwas added
6. 6
   Extraktionthe mixture was extracted with EtOAc
7. 7
   Trocknendried (MgSO4)
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe residue was chromatographed on a silica gel column
10. 10
    Wascheneluting with hexane:Et2O 1:2 to 0:1

Vorschrift

To a solution of 5-bromo-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine from step 54b (1.03 g, 3.0 mmol) in acetonitrile (20 mL) and triethylamine (12.5 mL) was added 4-vinylpyridine (0.65 mL, 6 mmol), palladium acetate (125 mg, 0.56 mmol) and tri-o-tolylphosphine (625 mg). The mixture was heated at reflux for 16 hours. The solvent was removed, and the residue was washed with saturated sodium bicarbonate was added to free the amine, and the mixture was extracted with EtOAc, dried (MgSO4), and concentrated. The residue was chromatographed on a silica gel column, eluting with hexane:Et2O 1:2 to 0:1 to afford the title compound (760 mg, 69%). MS (CI/NH3) m/z 368 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.43 (s, 9H), 2.35 (m, 2H), 3.90 (m, 2H), 4.20 (m, 1H), 4.40 (m, 1H), 4.55 (m, 1H), 7.10 (m, 1H), 7.2 (m, 1H), 7.38 (m, 2H), 7.45 (br s, 1H), 8.29 (m, 1H), 8.37 (s, 1H), 8.61 (m, 2H).

Quelle