Sodium Carbonate → 5-(4-Chlorophenyl)pyridin-2-amine

HRID 271643

Reaktionsgleichung

Reaktionsgleichung von HRID 271643
C([O-])([O-])=O.[Na+].[Na+].[NH2:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][N:9]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19](OB(O)O)=[CH:18][CH:17]=1>O1CCOCC1.CO.CCOC(C)=O.O>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:11]2[CH:12]=[CH:13][C:8]([NH2:7])=[N:9][CH:10]=2)=[CH:18][CH:17]=1

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 706222-Amino-5-bromopyridineHCID 17810664p-Chlorophenylboric acid

Produkt 1

HCID 132426445-(4-Chlorophenyl)pyridin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

300 mL (600 mmol) of a 2 M Na2CO3 solution and 3.45 g (3.0 mmol) tetrakis-triphenylphosphane-palladium are added successively to a solution of 53.5 g (300 mmol) 2-amino-5-bromopyridine and 50.0 g (313 mmol) 4-chlorophenylboric acid in 1.0 L 1,4-dioxane and 250 mL methanol under argon. The reaction mixture is stirred for 2.5 h at 110° C. The solvent is eliminated i.vac., the residue is taken up in EtOAc and water. The organic phase is dried over Na2SO4 and the solvent is eliminated i.vac. Further purification is carried out by column chromatography on silica gel (gradient: DCM to DCM/MeOH 20:1).

Aufarbeitung

  1. dry with materialThe organic phase is dried over Na2SO4
  2. customFurther purification

Quellen und Nachweise

ORD-Eintrag
ord-80e0d4f23fad482f85ed42d47a9067e4
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452911B2

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