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Water → 3-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methylsulfanyl-[2,3']bipyridine

HRID 228807
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 228807
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[C:6]([OH:15])=[CH:5][CH:4]=1.Cl[C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][CH:18]=1.O>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:28][O:27][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][C:23]=1[O:29][CH3:30])[N:20]=[CH:19][CH:18]=[C:17]2[O:15][C:6]1[C:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[N:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 962WaterHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 688293916-Methylsulfanyl-[2,3']bipyridin-3-ol

Produkt 1

HCID 577564963-(6,7-Dimethoxy-quinolin-4-yloxy)-6-methylsulfanyl-[2,3']bipyridineAusbeute 103,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 7239
1,2-Dichlorobenzene
Lösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

6-Methylsulfanyl-[2,3′]bipyridin-3-ol (13 mg), 4-chloro-6,7-dimethoxyquinoline (46 mg), and 4-dimethylaminopyridine (29 mg) were suspended in o-dichlorobenzene (2 ml), and the suspension was stirred at 140° C. for 4 hr. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-chloroform to give the title compound (25 mg, yield 91%).

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water and saturated brine
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-12833f2d3ef34d818c76a9c60a7798c6
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560558B2

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