Reaktion #313267

Reaktionsgleichung

3-Bromo-5-chloro-thieno[3,2-b]pyridine

8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine

n-BuLi

hexane

→

3-(3-bromo-5-chloro-thieno[3,2-b]pyridin-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

Ausbeute 3.0%

3-(5-chloro-thieno[3,2-b]pyridin-3-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

Ausbeute 2.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred at room temperature for 20 in
2. 2
   Sonstigethe reaction
3. 3
   Sonstigecap
4. 4
   TemperaturThe vial is heated at 80° C. overnight
5. 5
   FiltrationThe reaction mixture is filtered

Vorschrift

248 g of 3-Bromo-5-chloro-thieno[3,2-b]pyridine (1.0 mol) is dissolved in 2.0 l of dry THF and cooled to −78° C. 0.4 l of n-BuLi 2.5M in hexane (1.0 mol) is added slowly and stirred at −78° C. for 15 in. 2.0 l of 0.5M ZnCl2 in THF (1.0 mol) is added and stirred at room temperature for 20 in. 343 g of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (1.0 mol) and 37 g of PdCl2(dppf) (0.05 mol) are added and the reaction vial is capped with a Teflon cap. The vial is heated at 80° C. overnight. The reaction mixture is filtered and applied onto a silica-gel chromatography column (1st column; hexane AcOEt=10:1, 2nd column; CH3CN:CH2Cl2:Hexane=1:5:4) to give 16 mg of 3-(3-bromo-5-chloro-thieno[3,2-b]pyridin-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (3%) and 9 mg of 3-(5-chloro-thieno[3,2-b]pyridin-3-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (2%).

Quelle