Reaktion #51827

Reaktionsgleichung

sodium hydrogencarbonate

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

triethylamine

Methanesulfonyl chloride

→

4-(5-ethoxy-carbonyl-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
   Extraktionwas then extracted three times with chloroform
2. 2
   TrocknenThe combined organic layer was dried over anhydrous sodium sulfate
3. 3
   FiltrationThe desiccating agent was filtered off
4. 4
   Einengenthe filtrate was concentrated under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in benzene (1.0 mL)
6. 6
   workup.ADDITIONby adding
7. 7
   Temperatur1,8-diazabicyclo[5.4.0]-7-undecene (17 mg), and the resulting mixture was heated
8. 8
   Temperaturunder reflux for 1 hour
9. 9
   workup.ADDITIONA saturated aqueous ammonium chloride solution was poured into the reaction mixture, which
10. 10
    Extraktionwas then extracted three times with ethyl acetate
11. 11
    TrocknenThe combined organic layer was dried over anhydrous sodium sulfate
12. 12
    Filtrationafter which the desiccating agent was filtered off
13. 13
    Einengenthe filtrate was concentrated under reduced pressure
14. 14
    SonstigeThe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane-ethyl acetate=5:1)

Vorschrift

In methylene chloride (1.5 mL) were dissolved 1-(2,4-dichlorophenyl)-4-(3-ethoxycarbonyl-4-hydroxypiperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine (53 mg), triethylamine (34 mg) and a small amount of 4-dimethylaminopyridine. Methanesulfonyl chloride (25 mg) was added thereto and the resulting mixture was stirred at room temperature for 2 hours. A saturated aqueous sodium hydrogencarbonate solution was poured into the reaction mixture, which was then extracted three times with chloroform. The combined organic layer was dried over anhydrous sodium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in benzene (1.0 mL), followed by adding thereto 1,8-diazabicyclo[5.4.0]-7-undecene (17 mg), and the resulting mixture was heated under reflux for 1 hour. A saturated aqueous ammonium chloride solution was poured into the reaction mixture, which was then extracted three times with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, after which the desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane-ethyl acetate=5:1) to obtain 4-(5-ethoxy-carbonyl-1,2,3,6-tetrahydropyridin-1-yl)-1-(2,4-dichlorophenyl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine (27 mg).

Quelle