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Dimethylformamide → Diethyl 2-(2',3-dimethyl-2,4'-bipyridin-5-yl)malonate

HRID 1036226
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1036226
Cl[C:2]1[N:7]=[CH:6][C:5]([CH:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[CH3:19].[CH3:20][C:21]1[CH:26]=[C:25]([Sn](CCCC)(CCCC)CCCC)[CH:24]=[CH:23][N:22]=1.CN(C=O)C.[F-].[K+]>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:20][C:21]1[CH:26]=[C:25]([C:2]2[C:3]([CH3:19])=[CH:4][C:5]([CH:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][N:7]=2)[CH:24]=[CH:23][N:22]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 522689Potassium FluorideHCID 216605742-Methyl-4-(tributylstannyl)pyridineHCID 58447937Diethyl 2-(6-chloro-5-methylpyridin-3-yl)malonate

Produkt 1

HCID 58447640Diethyl 2-(2',3-dimethyl-2,4'-bipyridin-5-yl)malonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a reaction flask containing diethyl 2-(6-chloro-5-methylpyridin-3-yl)malonate 156-3 (1.00 g, 4.00 mmol), 2-methyl-4-(tributylstannyl)pyridine (1.53 g, 4.00 mmol) and Pd(PPh3)4 (440 mg, 0.4 mmol) under argon was added DMF (20 mL). The mixture was stirred at 120° C. for 10 hours. After the mixture was cooled down to room temperature, 1N KF aqueous solution was added to it and stirred for 15 minutes. The mixture was diluted with ethyl acetate and the two layers were separated. The organic layer was further washed with water and brine, dried over Na2SO4, concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 5% methanol in dichloromethane to give diethyl 2-(2′,3-dimethyl-2,4′-bipyridin-5-yl)malonate 156-4 as colorless oil. MS m/z 343.1 (M+1)

Aufarbeitung

  1. temperatureAfter the mixture was cooled down to room temperature
  2. stirringstirred for 15 minutes
  3. customthe two layers were separated
  4. washThe organic layer was further washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness by rotary evaporation
  7. customThe crude product was purified by silica gel flash chromatography
  8. washeluted with 5% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-86c859449bb04df8971b9629a5685351
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08546396B2

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