2-Chloro-6-phenyl-3-pyridinecarbonitrile

0.865 g of 2, 6-dichloro-nicotine and 1.021 g of 4, 4, 5, 5-tetramethyl-2-phenyl-1, 3, 2-dioxaborane were dissolved in 60 mlEthylene glycol dimethyl ether, 20 ml of an aqueous solution of sodium hydrogencarbonate (1 mole per liter) and 0.366 g of [1, 1'-bis (diphenylphosphineBased ferrocene] dichloride, the temperature was raised to 90 ° C under argon, and the mixture was heated for 6 hours. The reaction solution was separated, The aqueous phase was extracted with ethyl acetate and the organic phases were combined and washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filteredThe residue was purified by column chromatography (petroleum ether: ethyl acetate = 99: 1-95: 5, V / V) to give 0.680 g of a white solidRate of 63.4percent.Synthesis 1 C2-Chloro-6-phenylnicotinonitri]eA mixture of 2-chloro-6-phenylnicotinamide in acetic anhydride was allowed to reflux for 2 h. The reaction mixture was concentrated to dryness in vacuo. Ice-water was added to the reaction mixture. The mixture was partitioned between ethyl acetate and 10percent sodium hydrogencarbonate solution. The layers were then separated. The organic layer was dried ( gS0General procedure: To a solution of 9a-9h (10 mmol) in 10 mL of 1, 4-dioxane, POCl3(2.3 mL, 25 mmol) was added dropwise. The reaction mixture wasstirred at 80 C for 1 h. After cooled to room temperature, themixture was poured to 50 mL of ice water. 20 N NaOH aqueoussolutionwas added to adjust pH = 7. Solid was precipitated, filteredand purified by column chromatography (eluent: petroleum ether/ethyl acetate = 10:1) to provide the title compound. 1H NMR and13C NMR data of selected products are shown as follows.General procedure: A mixture of 10a-10k (1 mmol), methyl thioglycolate (159 mg, 1.5 mmol) and Et3N (152 mg, 1.5 mmol) in 10 mL of methanol was stirred at 80 C for 6-8 h. Methanol was removed under vacuum.The residuewas purified by column chromatography to provide thetitle compound.0.865 g of 2, 6-dichloro-nicotine and 1.021 g of 4, 4, 5, 5-tetramethyl-2-phenyl-1, 3, 2-dioxaborane were dissolved in 60 mlEthylene glycol dimethyl ether, 20 ml of an aqueous solution of sodium hydrogencarbonate (1 mole per liter) and 0.366 g of [1, 1'-bis (diphenylphosphineBased ferrocene] dichloride, the temperature was raised to 90 C under argon, and the mixture was heated for 6 hours. The reaction solution was separated, The aqueous phase was extracted with ethyl acetate and the organic phases were combined and washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filteredThe residue was purified by column chromatography (petroleum ether: ethyl acetate = 99: 1-95: 5, V / V) to give 0.680 g of a white solidRate of 63.4%.664 mg of To a solution of To a solution of

Molecular Weight:214.65
XLogP3:3.2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:214.0297759
Monoisotopic Mass:214.0297759
Topological Polar Surface Area:36.7
Heavy Atom Count:15
Complexity:252
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes