Potassium Carbonate → methyl 5-[(E)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethenyl]-2-(propan-2-yloxy)pyridine-4-carboxylate

HRID 577540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577540
Br[C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[N:6][CH:7]=1.[CH:16]([N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])=[CH2:17].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[O:28]=[C:19]1[C:20]2[C:21](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[O:23])[N:18]1/[CH:16]=[CH:17]/[C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[N:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-HCID 86723769Methyl 5-bromo-2-(propan-2-yloxy)pyridine-4-carboxylate

Produkt 1

HCID 86723770methyl 5-[(E)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethenyl]-2-(propan-2-yloxy)pyridine-4-carboxylateAusbeute 34,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418851HCID 178418851, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of methyl 5-bromo-2-(propan-2-yloxy)pyridine-4-carboxylate (112a, 3.40 g, 12.4 mmol) and N-vinylphthalimide (2.58 g, 14.9 mmol) in toluene (124 mL) was added K2CO3 (5.19 g, 37.2 mmol) followed by Pd(P(tBu)3)2 (0.400 g, 0.775 mmol). The reaction mixture was degassed and heated in a sealed tube at 110° C. for 18 hours. The reaction mixture was cooled to room temperature and filtered through CELITE®. H2O (100 mL) was added, the organic layer was separated and concentrated under vacuum, and the residue was purified by column chromatography (0-80%, ethyl acetate/heptanes) to give methyl 5-[(E)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethenyl]-2-(propan-2-yloxy)pyridine-4-carboxylate (112b, 1.56 g, 34%) as yellow solid.

Aufarbeitung

  1. customThe reaction mixture was degassed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered through CELITE®
  4. additionH2O (100 mL) was added
  5. customthe organic layer was separated
  6. concentrationconcentrated under vacuum
  7. customthe residue was purified by column chromatography (0-80%, ethyl acetate/heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-6a1c3afdff394f9980b3d6a1b061bff8
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040515B2

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