تفاعل #51827

معادلة التفاعل

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

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   استخلاصwas then extracted three times with chloroform
2. 2
   تجفيفThe combined organic layer was dried over anhydrous sodium sulfate
3. 3
   ترشيحThe desiccating agent was filtered off
4. 4
   تركيزthe filtrate was concentrated under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in benzene (1.0 mL)
6. 6
   workup.ADDITIONby adding
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   درجة الحرارة1,8-diazabicyclo[5.4.0]-7-undecene (17 mg), and the resulting mixture was heated
8. 8
   درجة الحرارةunder reflux for 1 hour
9. 9
   workup.ADDITIONA saturated aqueous ammonium chloride solution was poured into the reaction mixture, which
10. 10
    استخلاصwas then extracted three times with ethyl acetate
11. 11
    تجفيفThe combined organic layer was dried over anhydrous sodium sulfate
12. 12
    ترشيحafter which the desiccating agent was filtered off
13. 13
    تركيزthe filtrate was concentrated under reduced pressure
14. 14
    أخرىThe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane-ethyl acetate=5:1)

الإجراء التجريبي

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).

المصدر