Réaction #68511

Équation de réaction

cesium carbonate

phenylboronic acid

3,6-Dichloro-4-methylpyridazine

→

3-chloro-4-methyl-6-phenylpyridazine

Solvants

water

dioxane

Conditions de réaction

Traitement

1. 1
   ConcentrationThe reaction mixture was concentrated under vacuum
2. 2
   Autrethe remaining solid was triturated with water
3. 3
   AutreThe solid was collected on a glass frit
4. 4
   Lavagewashing well with water
5. 5
   AutreThe sample was purified by flash chromatography
6. 6
   Lavageeluting with 1:4 ethyl acetate/hexane

Mode opératoire

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.

Source