反应详情

温度

0 °C

45 ml 1.6M solution of n-butyllithium in hexane are added at −30° C. to a 10.2 g 2,2,6,6-tertamethylpiperidine in 100 ml THF and the mixture stirred at 0° C. for 30 min. After cooling to −75° C. 11.2 g 3-methoxy-6-pyridin-4-yl-pyridazine dissolved 300 ml THF are added and the solution stirred at −75° C. for 35 min. The cold (−75° C.) reaction mixture is subsequently added at a cold (−75° C.) solution of 18.3 g iodine in 400 ml THF (tetrahydrofuran) and stirred at −75° C. for 1.5 h. The reaction is quenched by adding 80 ml methanol/THF (1:1) at −75° C. and 300 ml saturated aqueous NaHCO3 at room temperature and extracted with dichloromethane. The organic layer is ished with 5% aqueous Na2S2O3 and saturated sodium chloride solution, dried (MgSO4) and the solvens removed. The crude product is purified by chromatography on silica gel to yield 14.4 g of 4-iodo-3-methoxy-6-pyridin-4-yl-pyridazine.

1. temperatureAfter cooling to −75° C
2. additionare added
3. stirringthe solution stirred at −75° C. for 35 min
4. customThe cold (−75° C.) reaction mixture
5. stirringstirred at −75° C. for 1.5 h
6. customThe reaction is quenched
7. additionby adding 80 ml methanol/THF (1:1) at −75° C.
8. extraction300 ml saturated aqueous NaHCO3 at room temperature and extracted with dichloromethane
9. dry with materialdried (MgSO4)
10. customthe solvens removed
11. customThe crude product is purified by chromatography on silica gel