Sodium Carbonate → 3-Chloro-5-phenylpicolinonitrile

HRID 340227

Reaktionsgleichung

Reaktionsgleichung von HRID 340227
[Cl:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6](Cl)[CH:7]=1.CC1(C)C(C)(C)OB([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.O>[Cl:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 570673Phenylboronic acid pinacol esterHCID 27696993,5-Dichloro-2-cyanopyridine

Produkt 1

HCID 668755223-Chloro-5-phenylpicolinonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21863594Toluene ethanolLösungsmittel

Versuchsvorschrift

A solution of 3,5-dichloropicolinonitrile (1.0 eq.), 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (1.0 eq.), tetrakis(triphenyl-phosphine)palladium (5 mol %), and 2N aqueous sodium carbonate solution (3.4 eq.) in toluene/ethanol (2:1, 0.04 M) was stirred at 100° C. for 2 hours, then 80° C. for 4 hours. After cooling to ambient temperature, the reaction content was diluted with ethyl acetate and water. The two phases were separated, and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give a white solid.

Aufarbeitung

  1. customThe two phases were separated
  2. extractionthe aqueous layer was extracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated en vacuo
  6. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)
  7. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-62e0b7d7a59f4a5aa69d5e0c58d390bf
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895577B2

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