Reaktion #2308286

Reaktionsgleichung

compound 5E

tert-Butyl 2-((3-bromo-6-phenylpyridazin-4-yl)methyl)acrylate

benzylamine

→

tert-butyl 8-benzyl-3-phenyl-5,6,7,8-tetrahydropyrido[2,3-c]pyridazine-6-carboxylate

Lösungsmittel

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITto 85° C. for 15 h
2. 2
   TemperaturThe reaction mixture was then cooled to room temperature
3. 3
   Sonstigethe solvent removed at reduced pressure
4. 4
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
5. 5
   Waschenwashed once with saturated sodium bicarbonate solution
6. 6
   ExtraktionThe organic extract
7. 7
   Trocknenwas dried over Na2SO4
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated under reduced pressure
10. 10
    SonstigePurification by silica gel chromatography (1:9 Ether/CH2Cl2)

Vorschrift

To a stirred solution of compound 5E, (0.140 g, 0.37 mmol) in 1.5 mL of isopropanol at room temperature under argon was added (in one portion) benzylamine (0.055 mL, 0.50 mmol). After 15 h, the reaction mixture was heated to 65° C. for 4 h and then to 85° C. for 15 h. The reaction mixture was then cooled to room temperature and the solvent removed at reduced pressure. The residue was dissolved in EtOAc and washed once with saturated sodium bicarbonate solution. The organic extract was dried over Na2SO4, filtered and evaporated under reduced pressure. Purification by silica gel chromatography (1:9 Ether/CH2Cl2) provided the title compound, tert-butyl 8-benzyl-3-phenyl-5,6,7,8-tetrahydropyrido[2,3-c]pyridazine-6-carboxylate, as a light yellow solid (0.084 g, 57%). MS [M+H]+: found 402.

Quelle