2,6-Dichloro-3-iodopyridine → (E)-2,6-dichloro-3-(2-ethoxyvinyl)pyridine

HRID 595754

Reaktionsgleichung

Reaktionsgleichung von HRID 595754
[Cl:1][C:2]1[C:7](I)=[CH:6][CH:5]=[C:4]([Cl:9])[N:3]=1.[CH2:10]([O:12]/[CH:13]=[CH:14]/B1OC(C)(C)C(C)(C)O1)[CH3:11]>O1CCOCC1.O.[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[Cl:1][C:2]1[C:7](/[CH:11]=[CH:10]/[O:12][CH2:13][CH3:14])=[CH:6][CH:5]=[C:4]([Cl:9])[N:3]=1

Komponenten

6

Edukt 2

HCID 27360022,6-Dichloro-3-iodopyridineHCID 219739081-Ethoxyethene-2-boronic acid pinacol ester

Produkt 1

HCID 90332512(E)-2,6-dichloro-3-(2-ethoxyvinyl)pyridineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178454861HCID 178454861, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a degassed solution of 2,6-dichloro-3-iodopyridine (3.0 g, 11 mmol) and (E)-2-(2-ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.2 g, 11 mmol) in 1,4-dioxane (20 mL) and water (1.0 mL) was added CS2CO3 (7.1 g, 22 mmol) and 1,1′-bis(di-tert-butylphosphino)ferrocene palladium chloride (357 mg, 0.54 mmol) under N2 protection. The resulting mixture was heated to 70° C. and stirred at this temperature overnight. The reaction was cooled, filtered through a pad of the celite and washed with ethyl acetate. The combined filtrate was evaporated in vacuo. The resulting residue was purified using column chromatography (eluted with 0-20% EtOAc/DCM) to provide (E)-2,6-dichloro-3-(2-ethoxyvinyl)pyridine (1.96 mg, yield: 86%). MS (M+H)+: 218.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. filtrationfiltered through a pad of the celite
  3. washwashed with ethyl acetate
  4. customThe combined filtrate was evaporated in vacuo
  5. customThe resulting residue was purified
  6. washcolumn chromatography (eluted with 0-20% EtOAc/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-f0084eab7f1f4f4582ed8aabfa1a8ce1
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09243002B2

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