Ethyl 2-chloroisonicotinate → Ethyl 2-(3,4,5-trimethoxyphenylethynyl)pyridine-4-carboxylate

HRID 1634898Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1634898
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]#[CH:14])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].Cl[C:16]1[CH:17]=[C:18]([CH:24]=[CH:25][N:26]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C.C(N(CC)CC)C.C(OCC)(=O)C.[Cu](I)I.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>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13]#[C:14][C:16]2[CH:17]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:24]=[CH:25][N:26]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Komponenten

8

Edukt 2

HCID 2762942Ethyl 2-chloroisonicotinateHCID 118302605-Ethynyl-1,2,3-trimethoxybenzene

Produkt 1

HCID 18674974Ethyl 2-(3,4,5-trimethoxyphenylethynyl)pyridine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

3,4,5-Trimethoxyphenylacetylene (1.80 g), ethyl 2-chloroisonicotinate (2.08 g) and copper iodide (71 mg) were dissolved in a mixed solvent of DMF (4 mL) and triethylamine (8 mL), and to the solution bis-(triphenylphosphine)palladium dichloride (0) (131 mg) was added, and the mixture was stirred at 45° C. for 4 hours under an argon atmosphere. The reaction mixture was diluted with ethyl acetate, washed with 2 M hydrochloric acid, water and saturated brine, dried over anhydrous sodium sulfate. After concentrating the reaction mixture under reduced pressure, the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1 to 3:1) to obtain the title compound.

Aufarbeitung

  1. washwashed with 2 M hydrochloric acid, water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationAfter concentrating the reaction mixture under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1 to 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-3d540c9f63c94badba83729f06af6a5a
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06509329B1

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