Reaktion #51825

Reaktionsgleichung

4-(4-cyano-1,2,3,6-tetrahydropyridin-1-yl)-1-(2,4-dichlorophenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine

sulfuric acid

→

title compound

4-(4-carbamoyl-1,2,3,6-tetrahydropyridin-1-yl)-1-(2,4-dichlorophenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONby adding
2. 2
   SonstigeThe reaction mixture was separated with ethyl acetate
3. 3
   Extraktiona saturated aqueous sodium hydrogencarbonate solution, and the aqueous layer was extracted twice with ethyl acetate
4. 4
   TrocknenThe combined organic layer was dried over anhydrous sodium sulfate
5. 5
   Filtrationthe desiccating agent was filtered off
6. 6
   Einengenafter which the filtrate was concentrated under reduced pressure
7. 7
   SonstigeThe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: chloroform-methanol=30:1)
8. 8
   Sonstigethe crystals precipitated
9. 9
   Waschenwere washed with ethyl acetate

Vorschrift

In methylene chloride (2.0 mL) was dissolved 4-(4-cyano-1,2,3,6-tetrahydropyridin-1-yl)-1-(2,4-dichlorophenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine (0.19 g), followed by adding thereto concentrated sulfuric acid (0.5 mL) under ice-cooling, and the resulting mixture was slowly heated to room temperature and then stirred overnight. The reaction mixture was separated with ethyl acetate and a saturated aqueous sodium hydrogencarbonate solution, and the aqueous layer was extracted twice with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate and the desiccating agent was filtered off, after which the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: chloroform-methanol=30:1) and the crystals precipitated were washed with ethyl acetate to obtain the title compound (0.10 g).

Quelle