Sodium Carbonate → 4-[4-Nitro-3-(propan-2-yloxy)phenyl]pyridine

HRID 518794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 518794
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH:12]([CH3:14])[CH3:13])[CH:3]=1.[N:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:18]2[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=2)=[CH:3][C:4]=1[O:11][CH:12]([CH3:14])[CH3:13])([O-:10])=[O:9]

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 226243214-Bromo-2-isopropoxy-1-nitro-benzene

Produkt 1

HCID 866979634-[4-Nitro-3-(propan-2-yloxy)phenyl]pyridineAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 10.0 g of 4-bromo-1-nitro-2-(propan-2-yloxy)benzene, 5.78 g of 4-pyridylboronic acid, 12.2 g of sodium carbonate and 1.0 g of bis(triphenylphosphine)dichloropalladium, in 200 ml of dioxane and 35 ml of water, is heated at 110° C. (bath) for 9 h. The mixture is diluted with ethyl acetate and water. The aqueous phase is extracted twice with ethyl acetate and then with dichloromethane. The combined organic phases are dried over magnesium sulfate and concentrated under vacuum. The residue is purified on 330 g of silica, elution being carried out with ethyl acetate/heptane (1/1 to 4/1), so as to obtain 7.35 g of 4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridine in the form of a pale yellow solid.

Aufarbeitung

  1. extractionThe aqueous phase is extracted twice with ethyl acetate
  2. dry with materialThe combined organic phases are dried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue is purified on 330 g of silica, elution

Quellen und Nachweise

ORD-Eintrag
ord-2d5085d39a9b406d8bd05ef6b23f24e2
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115140B2

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