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1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 44537962, Verbindung

HRID 655352
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 655352
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:14]=1.Br.Br[CH2:25][C:26]([C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1)=O.C1CCN2C(=NCCC2)CC1>C(#N)C>[N:31]1[CH:32]=[CH:33][C:28]([C:26]2[CH2:25][O:21][C:20](=[O:22])[C:19]=2[C:16]2[CH:15]=[CH:14][C:13]([O:12][CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)=[CH:18][CH:17]=2)=[CH:29][CH:30]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27762394-(Bromoacetyl)pyridine hydrobromideHCID 145002352-(4-(Quinolin-2-ylmethoxy)phenyl)acetic acid

Produkt 1

HCID 44537962HCID 44537962, VerbindungAusbeute 15,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-(quinolin-2-ylmethoxy)phenyl)acetic acid (3.0 g, 0.01 mol) in acetonitrile (40 mL) were added TEA (1.3 mL, 0.01 mol) and 2-bromo-1-(pyridin-4-yl)ethanone hydrobromide (2.86 g, 0.01 mol) at RT under an inert atmosphere. The reaction mixture was stirred for 1 h followed by addition of DBU (46.6 g, 0.03 mol) at 0° C. and stirring was continued for another 2 h at 0° C. The reaction mixture was quenched with HCl (1 N), aqueous layer was basified with NaHCO3 solution and extracted with DCM (2×50 mL). The combined organic layers were washed with water, dried over Na2SO4 and concentrated in vacuo to obtain the crude product. The crude product was purified via silica gel column chromatography eluting with 25% EtOAc in hexanes to afford 4-(pyridin-4-yl)-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-one (600 mg, 15%) as a solid.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for another 2 h at 0° C
  3. customThe reaction mixture was quenched with HCl (1 N), aqueous layer
  4. extractionextracted with DCM (2×50 mL)
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto obtain the crude product
  9. customThe crude product was purified via silica gel column chromatography
  10. washeluting with 25% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-651f0d0cd0054914a5d02c6a89579ac9
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08071595B2

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