Reaktion #1487780

Reaktionsgleichung

8-Chloro-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole

potassium phosphate

4-(2-Bromo-1-phenylvinyl)pyridine

L-proline

→

(E)-8-chloro-2-methyl-5-(2-phenyl-2-(pyridin-4-yl)vinyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe mixture purged with nitrogen for 2 min
2. 2
   workup.ADDITIONWater was added
3. 3
   Filtrationthe solid mass was filtered under vacuum
4. 4
   SonstigeThe crude compound was purified on silica gel (100-200 mesh)
5. 5
   SonstigeThe compound was further purified through reverse phase HPLC

Vorschrift

4-(2-Bromo-1-phenylvinyl)pyridine (310 mg, 1.1 mmol) was dissolved in DMF (5 mL) and potassium phosphate (424 mg, 2 mmol) was added followed by copper (I) iodide (19 mg, 0.1 mmol) and L-proline (23 mg, 0.2 mmol). 8-Chloro-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole (220 mg, 1 mmol) was added and the mixture purged with nitrogen for 2 min. The reaction mixture was stirred at 85° C. overnight. Water was added and the solid mass was filtered under vacuum. The crude compound was purified on silica gel (100-200 mesh) using 0-10% MeOH:DCM as eluent. The compound was further purified through reverse phase HPLC. Yield: 20 mg (TFA salt). 1H NMR (CDCl3, TFA salt) δ (ppm): 8.78 (d, 2H), 7.64 (d, 2H), 7.40-7.28 (m, 5H), 7.10 (m, 2H), 6.92 (d, 2H), 4.65 (m, 1H), 4.0 (m, 1H), 3.60 (m, 1H), 3.05 (m, 1H), 2.84 (s, 3H), 2.76 (m, 2H).

Quelle