[2,2′-Bipyridine]-6-carboxylic acid

(1) (S)-6-(4-(tert-butyl)-1-(p-tolyl)-4, 5-dihydro-1H-imidazol-2-yl)-2, 2'-bipyridine preparation: 2, 2-bipyridyl-6-carboxylic acid (10 mmol)In thionyl chloride solution (5 mL)Reflow reaction for 8 h, The excess thionyl chloride was removed by rotary evaporation to give a pale yellow oil.Dissolve it in an anhydrous dichloromethane solution, In ice bath conditions, Adding and dissolving L-tert-leucine (11 mmol, 1.29 g) andTriethylamine (30mmol, 4.2 mL)In the anhydrous dichloromethane solution, after completion of the dropwise addition, the reaction was allowed to proceed at room temperature overnight.After completion of the reaction, the reaction was spun dry, ethyl acetate was added, and the insoluble material was removed by filtration.After the filtrate was spun dry, continue to add thionyl chloride (5 mL) under reflux for 8 h.The excess thionyl chloride was removed by rotary evaporation to give a reddish brown oil.Dissolve it in an anhydrous dichloromethane solution under ice bath conditions, Adding dropwise to the solution of p-toluidine (11 mmol, 1.2 g) andTriethylamine (60 mmol, 8 mL)In anhydrous dichloromethane solution, After stirring at room temperature overnight, Add 10% aqueous sodium hydroxide solution (35 mL), Stirring was continued for 8-12 h at room temperature. After completion, the mixture was separated and the aqueous phase was extracted with dichloromethane three times.The organic phase is dried over anhydrous magnesium sulfate and suction filtered.Spin-drying and column chromatography (eluent ratio PE/EA = 3/1 to 1/10) gave the corresponding NNN' ligand.Brown solid; Yield: 52%;(1) Preparation of (S)-6-(4-benzyl-1-(p-tolyl)-4, 5-dihydro-1H-imidazol-2-yl)-2, 2'-bipyridine:2, 2-bipyridyl-6-carboxylic acid (10 mmol) was refluxed in thionyl chloride solution (5 mL) for 8 h, and the excess thionyl group was removed by rotary distillation.Chlorine obtained as a pale yellow oil, which was dissolved in anhydrous methylene chloride, and then, in ice bath, was added dropwise to dissolve L-phenylalaninol (11 mmol, 1.82 g) and triethylamine (30 mmol, 4.2 In an anhydrous dichloromethane solution of mL), after the addition is completed, The reaction was allowed to proceed overnight at room temperature. After the reaction was completed, the reaction mixture was spun dry, ethyl acetate was added, and the insoluble material was removed by filtration, and the filtrate was dried.Continue to add thionyl chloride (5 mL) under reflux for 8 h, and remove excess thionyl chloride by rotary distillation to give a reddish brown oil.Dissolve it in an anhydrous dichloromethane solution and add dropwise p-toluidine (11 mmol, 1.2 g) in an ice bath.And triethylamine (60mmol, 8mL) in anhydrous dichloromethane, after working overnight at room temperature, then add 10% sodium hydroxideThe aqueous solution (35 mL) was stirred at room temperature for 8-12 h. After completion, the mixture was separated and the aqueous phase was extracted three times with dichloromethane.Add anhydrous magnesium sulfate, filter by suction, spin dry, and separate by column chromatography (eluent ratio PE/EA = 3/1~1/10) to obtain correspondingNNN' ligand. Brown solid; yield 56%;(1) Preparation of (S)-6-(4-isopropyl-1-(p-tolyl)-4, 5-dihydro-1H-imidazol-2-yl)-2, 2'-bipyridine:2, 2-bipyridyl-6-carboxylic acid (10 mmol)In thionyl chloride solution (5 mL)Reflow reaction for 8 h, The excess thionyl chloride was removed by rotary evaporation to give a pale yellow oil.Dissolve it in an anhydrous dichloromethane solution, In ice bath conditions, Adding and dissolving L-prolinol (11 mmol, 1.13 g) andTriethylamine (30mmol, 4.2 mL)In the anhydrous dichloromethane solution, after completion of the dropwise addition, the reaction was allowed to proceed at room temperature overnight.After completion of the reaction, the reaction was spun dry, ethyl acetate was added, and the insoluble material was removed by filtration.After the filtrate was spun dry, continue to add thionyl chloride (5 mL)Reacted under reflux for 8 h, The excess thionyl chloride was removed by rotary evaporation to give a reddish brown oil.Dissolve it in an anhydrous dichloromethane solution, In an ice bath, the solution was dissolved in p-toluidine (11 mmol, 1.2 g).And triethylamine (60 mmol, 8 mL)In anhydrous dichloromethane solution, After stirring at room temperature overnight, Add 10% aqueous sodium hydroxide solution (35 mL), Stirring was continued for 8-12 h at room temperature. After completion, the mixture was separated and the aqueous phase was extracted with dichloromethane three times.Drying with anhydrous magnesium sulfate, suction filtration, spin-drying and column chromatography (eluent ratio PE/EA = 3/1 to 1/10) gave the corresponding NNN' ligand.Brown solid; yield: 50%;

Molecular Weight:200.19
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:200.058577502
Monoisotopic Mass:200.058577502
Topological Polar Surface Area:63.1
Heavy Atom Count:15
Complexity:233
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes