Potassium Carbonate → 4-Bromo-5-(1-methoxyimino-indan-5-yl)-furan-2-carbaldehyde

HRID 271514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271514
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[O:9])[O:5][C:6]=1Br.[CH3:10][O:11][N:12]=[C:13]1[C:21]2[C:16](=[CH:17][C:18](B(O)O)=[CH:19][CH:20]=2)[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[O:9])[O:5][C:6]=1[C:18]1[CH:17]=[C:16]2[C:21](=[CH:20][CH:19]=1)[C:13](=[N:12][O:11][CH3:10])[CH2:14][CH2:15]2

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 10852284,5-Dibromofuran-2-carbaldehydeHCID 734146811-Methoxyimino-indan-5-boronic acid

Produkt 1

HCID 867607594-Bromo-5-(1-methoxyimino-indan-5-yl)-furan-2-carbaldehydeAusbeute 35,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A degassed mixture of the product of Step 3 (6.6 g, 26.0 mmol), 1-methoxyimino-indan-5-boronic acid (5.3 g, 26.0 mmol) and potasium carbonate (28 g, 202 mmol) in ethylene glycol dimethyl ether (150 ml) and water (75 ml) was treated with bis(triphenylphosphine) palladium (II) chloride (1.05 g, 1.5 mmol), then heated under reflux for 6 hours. After cooling to room temperature, the mixture was filtered through celite and the filtrate diluted with water and ethyl acetate. The organic phase was separated, washed with water and brine, dried, concentrated in vacuo and the residue purified by silica gel chromatography eluting with dichloromethane to give the title compound (3.06 g, 35%); MS(ES+) m/e 334/336 [M+H]+.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. filtrationthe mixture was filtered through celite
  4. additionthe filtrate diluted with water and ethyl acetate
  5. customThe organic phase was separated
  6. washwashed with water and brine
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customthe residue purified by silica gel chromatography
  10. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-98a5e996fa7a46de8b85200e8537352c
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452906B2

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