4,4′-Dinonyl-2,2′-bipyridine

White or off-white powder

Diisopropylamine (28.0 mL, 0.160 mol, 2.66 equiv.) was dissolved in dry THF (60 mL) under an argon atmosphere. n-butylithium (107.0 mL, 0.160 mol, 2.66 equiv.) was added dropwise at 0 °C and the solution was stirred for 1 h. Afterwards, a solution of 4, 4′-dimethyl-2, 2′-bipyridine (11.0 g, 0.060 mol, 1 eq.) in dry THF (300 mL) was slowly added and the orange solution was stirred for 3 h. The reaction mixture was kept at 0 °C and bromooctane (28.0 mL, 0.160 mol, 2.66 equiv.) in dry THF (20 mL) was added. The reaction mixture was then allowed to warm to room temperature. After stirring for 12 h the reaction was quenched first with water (20 mL), then poured into an ice/ water mixture and extracted with diethylether. The resulting yellow oil was recrystallized from hexane, redissolved in DCM, extracted with diluted NaOH, dried over MgSOGeneral procedure: To a sonicated solution of ruthenium trichloride hydrate (0.1 g, 0.48 mmol) in 5 ml anhydrous ethanol, a solution of 4, 4'-dialkyl-2, 2'-bipyridine (1.44 mmol in 10 ml absolute ethanol (0.394 g ofC5 for RC5, 0.434 g of C6 for RC6, 0.469 g of C7 for RC7, 0.506 gof C8 for RC8, 0.543 g of C9 for RC9) was added drop wise. Thereaction mixture was refluxed for 2 hr at 80 C. The resultingorange coloured solution was cooled at room temperature (26 C)and the solvent was reduced by rotatary evaporator. The pure productwas separated by silica gel column chromatography using 1:1ethyl acetate/petroleum ether as eluent solvent. The unreactedligands eluted as a first fraction (monitored by TLC) followed byorange band of the main product. The orange band was concentratedby reducing the solvent and further precipitated using2 ml saturated ammonium hexafluorophosphate solution inmethanol. The dark orange coloured precipitate was filtered andthe residue was washed with millipore water. The precipitatewas dried in vacuum (Scheme 2).

Molecular Weight:408.7
XLogP3:10.7
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:17
Exact Mass:408.350449412
Monoisotopic Mass:408.350449412
Topological Polar Surface Area:25.8
Heavy Atom Count:30
Complexity:347
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes