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| general procedure for Nickel(0)-mediated coupling of halomethoxy pyridine to dimethoxybipyridine: To a solution of 7.15g (30mmmol) of NiCl2.6H2O and 31.5g (120mmol) of triphenyl phosphane in 200ml of DMF under nitrogen atmosphere(1bar) is added 1.97g (30mmol) of Zn dust, the reaction mixture is stirred for 1h at 50℃. Subsequently 30mmol of halogmethoxy pyridine ( or the mixture of halomethoxy pyridines) is added and the mixture is stirred for 5-120 h (see Table 1) at 50℃. The reaction mixture is poured into 800ml of half concentrated NH3 and stirred for 1h and the aqueous phase is extracted 3 times with each of 150ml of CHCl3. The combined organic phase was completely evaporated and the residue is taken up in 300ml of CHCl3. The solution is extracted 5 times with each of 100ml of half concentrated HCl. The combined aqueous phase is extracted with 50ml of CHCl3 and subsequently made alkaline with aqueous Na2CO3 solution. The aqueous phase is extracted 4 times with each of 100ml of CHCl3, the combined organic phase was dried with Na2SO4 and concentrated to dryness. The residue is purified chromatographically on silica gel with the eluent MDC/2% MeOH or directly recrystallized from ethanol. |
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