Cesium carbonate → 3-Chloro-4-methyl-6-phenylpyridazine

HRID 40233

Reaktionsgleichung

Reaktionsgleichung von HRID 40233
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[CH3:8].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][C:7]=1[CH3:8]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 879233,6-Dichloro-4-methylpyridazine

Produkt 1

HCID 1199993-Chloro-4-methyl-6-phenylpyridazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3,6-Dichloro-4-methylpyridazine (1.00 g, 6.1 mmol) was mostly dissolved in dioxane (22.5 mL) then added phenylboronic acid (0.82 g, 6.7 mmol), PdCl2(dppf)-CH2Cl2Adduct (0.25 g, 0.31 mmol) and a solution of cesium carbonate (6.0 g, 18 mmol) in water (7.5 mL). The reaction mixture was heated at 80° C. for 6 hours. The reaction mixture was concentrated under vacuum and the remaining solid was triturated with water. The solid was collected on a glass frit, washing well with water. The sample was purified by flash chromatography eluting with 1:4 ethyl acetate/hexane to afford 3-chloro-4-methyl-6-phenylpyridazine as an off-white solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe remaining solid was triturated with water
  3. customThe solid was collected on a glass frit
  4. washwashing well with water
  5. customThe sample was purified by flash chromatography
  6. washeluting with 1:4 ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-5062e03fd1f04c97a5f51369e0c1f098
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524900B2

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