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N-bromobutanimide → cis-4-[5-Bromo-6-(2-methyl-3-furanyl)-2-pyridinyl]-2,6-dimethylmorpholine

HRID 2278426
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2278426
[Br:1]N1C(=O)CCC1=O.[CH3:9][C@H:10]1[O:15][C@@H:14]([CH3:16])[CH2:13][N:12]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:27]=[CH:26][O:25][C:24]=3[CH3:28])[N:18]=2)[CH2:11]1>C(Cl)(Cl)Cl>[Br:1][C:20]1[CH:21]=[CH:22][C:17]([N:12]2[CH2:11][C@H:10]([CH3:9])[O:15][C@H:14]([CH3:16])[CH2:13]2)=[N:18][C:19]=1[C:23]1[CH:27]=[CH:26][O:25][C:24]=1[CH3:28]
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Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 67514523cis-2,6-Dimethyl-4-[6-(2-methyl-3-furanyl)-2-pyridinyl]morpholine

Produkt 1

HCID 86702424cis-4-[5-Bromo-6-(2-methyl-3-furanyl)-2-pyridinyl]-2,6-dimethylmorpholine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N-Bromosuccinimide (137 mg, 0.771 mmol) was added portionwise to a solution of cis-2,6-dimethyl-4-[6-(2-methyl-3-furanyl)-2-pyridinyl]morpholine (210 mg, 0.771 mmol) in chloroform (7 mL) at 0° C. The reaction was stirred at 0° C. for 1 hour. Crude LC/MS showed desired product can be seen and no starting material left, so the reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (10 mL), brine (10 mL), water (10 mL) and brine (10 mL). The organic layer was dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was dissolved in dichloromethane (˜10 ml) and purified on silica by a Biotage SP4 chromatographic system (40+S cartridge, eluted with 0-100% ethyl acetate in isohexanes). Fractions containing pure product were combined and concentrated under reduced pressure to give the title compound as a colourless oil (280 mg, 0.678 mmol, 88% yield). LC/MS [M+H]+=351/353.

Quellen und Nachweise

ORD-Eintrag
ord-4e7f2f46809342f88c9e5fe92b2827e7
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09133178B2

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