6,6'-二甲基-2,2'-联吡啶-4,4'-二甲酸甲酯的合成与表征

以6-甲基-2-羟基吡啶-4-甲酸甲酯为起始原料,经酯化反应制备2-甲基-6-(对甲苯磺酰氧基)吡啶-4-甲酸甲酯,使其在过渡金属镍络合物催化作用下自身偶联合成6,6'-二甲基-2,2'-联吡啶-4,4'-二甲酸甲酯,通过改变投料比例、反应温度及投料顺序获得最佳反应条件,收率77%。经核磁共振、红外光谱、质谱及差示扫描热量法等对分子结构进行了表征,验证了合成方法的可靠性。该结构能够满足均相时间分辨荧光免疫分析螯合剂中间体的需求。目前,它已成功用于均相时间分辨荧光免疫分析。

Synthesis and Characterization of Dimethyl 6,6'-Dimethyl-[2,2'-bipyridine]-4,4'-dicarboxylate

Dimethyl 6,6'-dimethyl-[2,2'-bipyridine]-4,4'-dicarboxylate was synthesized in two steps from methyl 6-methyl-2-hydroxypyridine-4-carboxylate. The first step was the preparation of methyl 2-methyl-6-[(p-toluenesulfonyl)oxy]pyridine-4-carboxylate by esterification. The second step was to prepare the target product by nickel complex catalyzed homocoupling reaction. Several other factors which affected the reaction such as material proportion, reaction temperature and addition order were investigated. When the reaction was carried out under the optimal conditions, 77% yield was achieved. The products were characterized by nuclear magnetic resonance(NMR), Fourier transform infrared spectrometer(FTIR), mass spectrometry(MS) and differential scanning calorimetry(DSC) to prove the reliability of the synthetic method. This structure can fully satisfy the need of chelating agent intermediate for homogeneous time-resolved fluoroimmunoassay(HTRF), which has been succeeded in prectical applications.