반응 #1969292

반응 방정식

sodium methoxide

methanol

trimethylsulfoxonium iodide

sodium hydride

6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridine-3-carbaldehyde

ammonium chloride

→

title compound

수율 28.0%

2-[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]-2-methoxyethanol

수율 28.0%

용매

Water

dimethylsulfoxide

dimethylsulfoxide

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 1 hr
2. 2
   추출the mixture was extracted with ethyl acetate
3. 3
   세척The ethyl acetate layer was washed with saturated brine
4. 4
   건조dried (MgSO4)
5. 5
   농축concentrated
6. 6
   기타to give a crude product (1.0 g)
7. 7
   기타The obtained crude product
8. 8
   workup.STIRRINGthe mixture was stirred for 2 hr
9. 9
   추출the mixture was extracted with ethyl acetate
10. 10
    세척The ethyl acetate layer was washed with saturated brine
11. 11
    건조dried (MgSO4)
12. 12
    농축concentrated
13. 13
    기타to give a pale-yellow amorphous solid from a fraction
14. 14
    세척eluted with ethyl acetate
15. 15
    기타The obtained pale-yellow amorphous solid was purified by preparative HPLC

실험 절차

To a solution of trimethylsulfoxonium iodide (947 mg) in dimethylsulfoxide (5 mL) was added sodium hydride (oil, about 60%) (129 mg) and the mixture was stirred at room temperature m for 1 hr. The reaction mixture was added dropwise to a solution of 6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridine-3-carbaldehyde (1 g) in dimethylsulfoxide (5 mL) and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give a crude product (1.0 g). The obtained crude product was dissolved in methanol (10 mL), sodium methoxide (64 mg) was added at room temperature, and the mixture was stirred for 2 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to give a pale-yellow amorphous solid from a fraction eluted with ethyl acetate. The obtained pale-yellow amorphous solid was purified by preparative HPLC to give the title compound (310 mg, yield 28%) as a colorless amorphous solid. MS: 511 (MH+).

출처