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Triethylamine → 2,8-dimethyl-7-(4-methyl-1H-pyrazol-1-yl)quinoline

HRID 339019
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 339019
Br[C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:13])=[N:9]2)=[CH:4][CH:3]=1.C[N:15]1[CH:19]=[C:18](B2OC(C)(C)C(C)(C)O2)[CH:17]=[N:16]1.[F-].[Cs+].[CH2:31](N(CC)CC)C>C(O)(C)C.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]>[CH3:13][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[C:11]([CH3:12])[C:2]([N:16]3[CH:17]=[C:18]([CH3:31])[CH:19]=[N:15]3)=[CH:3][CH:4]=2)[N:9]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 25953Cesium fluorideHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 455994557-Bromo-2,8-dimethylquinoline

Produkt 1

HCID 709842262,8-dimethyl-7-(4-methyl-1H-pyrazol-1-yl)quinolineAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator
HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a sealed tube a mixture of 7-bromo-2,8-dimethylquinoline (0.60 g, 2.54 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.06 g, 5.08 mmol), PdCl2(dppf)*dcm (0.208 g, 0.254 mmol), CsF (1.00 g, 6.61 mmol) and triethylamine (0.531 mL, 3.81 mmol) in isopropyl alcohol (17 mL) was heated at 100° C. on an oil bath for 6 hours. The mixture was cooled to ambient temperature and partitioned between water (25 mL) and ethyl acetate (50 mL). The solids were removed by filtration through a pad of Celite and washed with additional ethyl acetate. The layers were separated and the organic layer washed with brine and dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Biotage 25M; 25% ethyl acetate/hexane) to afford 2,8-dimethyl-7-(4-methyl-1H-pyrazol-1-yl)quinoline (0.60 g, 91%).

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. custompartitioned between water (25 mL) and ethyl acetate (50 mL)
  3. customThe solids were removed by filtration through a pad of Celite
  4. washwashed with additional ethyl acetate
  5. customThe layers were separated
  6. washthe organic layer washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography (Biotage 25M; 25% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7dbaf9571cd44f3aabf29fabc18452e5
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08889704B2

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