56100-20-0 5-Methyl-2,2′-bipyridine 11073848, acatalyst-ligand compound, is more and more widely used in various fields.
With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.56100-20-0,5-Methyl-2,2′-bipyridine,as a common compound, the synthetic route is as follows.,56100-20-0
To a mixture of dry diisopropylamine (1.0 mL, 7.1 mmol) and dry THF (50 mL) was added dropwise n-butyllithium (1.6 M hexane solution, 3.8 mL, 6.1 mmol) at -78 C under a nitrogen atmosphere. The solution was stirred for 30 min and 6 (681 mg, 4.00 mmol) in dry THF (15 mL) was added at -78 C. The solution was stirred for 1 h and 1,4-dibromobutane (4.32 g, 20.0mmol) in dry THF (15 mL) was added. The solution was allowed to warm up to room temperature and stirred overnight. The reaction mixture was washed with aqueous sodium hydrogen carbonate and brine. The solution was dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was separated by column chromatography on aluminium oxide (hexane/dichloromethane = 3/1 (v/v)) to give 7 as a white solid (964 mg, 79%). 7: mp 31 C; 1H NMR (300 MHz,CDCl3): 8.67 (d, 1H, J = 4.8 Hz), 8.51 (d, 1H, J = 2.1 Hz), 8.36 (d, 1H, J = 8.0 Hz), 8.31 (d, 1H, J = 8.1 Hz), 7.81 (td,1H, J = 7.7, 1.6 Hz), 7.64 (dd, 1H, J = 8.1, 2.0 Hz), 7.31-7.29 (m, 1H), 3.41 (t, 2H, J = 6.7 Hz), 2.70 (t, 2H, J = 7.6 Hz), 1.91 (quintet, 2H, J = 7.1 Hz), 1.70 (quintet, 2H, J = 7.6 Hz), 1.57-1.49 (m, 2H); 13C NMR (75 MHz, CDCl3): 156.2, 154.0,149.3, 149.2, 137.7, 136.9, 136.8, 123.5, 120.8, 120.7, 33.6,32.7, 32.5, 30.2, 27.7; MS (EI+): m/z 304 [M+]; IR (KBr,cm-1): 3067(m), 3053(m), 3011(m), 2962(m), 2943(s), 2928(s), 2866(s), 1585(s), 1574(m), 1557(s), 1460(s), 1429(s), 1392(m), 1350(w), 1304(w), 1258(m), 1230(m), 1205(m), 1190(w), 1148(w), 1092(w), 1065(w), 1042(w), 1030(m), 1013(m), 991(m), 860(s), 808(m), 785(s), 752(s), 737(m), 727(m), 640(s), 606(s); HRMS (EI+): m/z calcd for C15H1779BrN2 [M+]: 304.0575; found: 304.0577.
56100-20-0 5-Methyl-2,2′-bipyridine 11073848, acatalyst-ligand compound, is more and more widely used in various fields.
Reference£º
Article; Ninomiya, Yoshikazu; Kozaki, Masatoshi; Suzuki, Shuichi; Okada, Keiji; Bulletin of the Chemical Society of Japan; vol. 87; 11; (2014); p. 1195 – 1201;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI