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Water → 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)-quinoline

HRID 1890929
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1890929
Br[C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:14][N:15]1[CH:19]=[C:18](B2OC(C)(C)C(C)(C)O2)[CH:17]=[N:16]1.C([O-])([O-])=O.[Na+].[Na+].O>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[CH3:13][O:12][C:11]1[C:2]([C:18]2[CH:17]=[N:16][N:15]([CH3:14])[CH:19]=2)=[C:3]2[C:8](=[CH:9][CH:10]=1)[N:7]=[CH:6][CH:5]=[CH:4]2
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Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 184141285-Bromo-6-methoxyquinoline

Produkt 1

HCID 689020116-methoxy-5-(1-methyl-1H-pyrazol-4-yl)-quinolineAusbeute 139,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 5-bromo-6-methoxy-quinoline (6.5 g, 0.021 mol), 1-methyl-4-pyrazoleboronic acid pinacol ester (8.74 g, 0.042 mol), Na2CO3 (6.687 g, 0.063 mol), Pd(dppf)Cl2 (1.7 g, 0.001 mol), H2O (32 mL) and 1,4-dioxane (80 mL) was heated at 100° C. overnight. After cooling down to room temperature, most of the dioxane was removed under vacuo. The mixture was diluted with ethyl acetate (50 mL) and brine (50 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (2×50 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give compound 7 g of 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)-quinoline.

Aufarbeitung

  1. customwas removed under vacuo
  2. additionThe mixture was diluted with ethyl acetate (50 mL) and brine (50 mL)
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (2×50 mL)
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7a8e3d7d31174730aec02b644aae89f3
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08507489B2

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