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With oxygen In 1,2-dichloro-benzene at 120℃; for 6h; Schlenk technique;
95%
With C23H22ClNORu In dichloromethane at 20℃; for 9h;
7 Example 7: Catalytic oxidation reaction
Using the catalyst prepared in Example 1 to catalyze the oxidation of alkyl pyridine compounds:The alkyl pyridine compound (1.0mmol) and the ruthenium complex Ru (0.02mmol)Dissolve in 3mL of dichloromethane, react with air as oxidant at room temperature for 9 hours,After the end, the concentrated reaction solution is directly separated by silica gel column chromatography, and dried to the same quality.The corresponding product C12H9NO (yield 95%) is obtained, and the reaction formula is:
92%
With N-hydroxyphthalimide; oxygen; cobalt(II) diacetate tetrahydrate In acetic acid butyl ester for 12h; Heating;
65%
With tert.-butylhydroperoxide; ZnCrCO3-HTlc In <i>tert</i>-butyl alcohol for 24h; Heating;
54%
With tert.-butylnitrite; N-hydroxyphthalimide; oxygen In benzonitrile at 80℃; for 24h; Schlenk technique;
50%
With tert.-butylhydroperoxide; copper(l) iodide In acetonitrile at 20℃;
50%
With tert.-butylhydroperoxide; copper(l) iodide In acetonitrile at 20℃;
37%
With palladium on activated charcoal; water; caesium carbonate In N,N-dimethyl acetamide at 110℃; for 48h; Inert atmosphere; Sealed tube;
> 99 %Chromat.
With tert.-butylhydroperoxide; water; oxygen at 20℃; for 7h;
R.1 REFERENCE EXAMPLE 1
REFERENCE EXAMPLE 1 To dimethylsulfoxide (40 ml) was added dropwise sodium hydride (1.0 g), and the mixture was heated at 80° C. for 30 minutes. The reaction mixture was cooled to room temperature, to which was added 5-carboxypentyltriphenyl phosphonium bromide (9.5 g, 21 mmole), and the mixture was stirred for 5 minutes. To the reaction mixture was added a tetrahydrofuran solution (10 ml) of 3.7 g (0.02 mole) of 3-benzoylpyridine. The mixture was stirred for 30 minutes at room temperature, followed by addition of water (100 ml), which was subjected to extraction twice with ethylacetate (50 ml). The aqueous layers were combined and adjusted to pH 6 with 2N HCl, which was subjected to extraction with ethyl acetate. The organic layers were combined and washed with water and dried (magnesium sulfate). The solvent was then evaporated and the residue was subjected to a silica-gel chromatography using ethanol-ethyl acetate (1:5) as the eluent to yield (E)+(Z)-7-(3-pyridyl)-7-phenyl-6-heptenoic acid (A-3, I-4 in Table 10) (4.5 g 79%).
With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 100℃; for 6h;
Typical procedure for carbonylative coupling with aryl bromides:
General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane).
(2'-chloro-[1,1'-biphenyl]-2-yl)(phenyl)(pyridin-3-yl)methanol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Stage #1: 2-bromo-2’-chloro-1,1’-biphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: 3-Benzoylpyridine In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere;
8.1 Synthesis of (2'-chloro-[1,1'-biphenyl]-2-yl) (phenyl)(pyridin-3-yl)methanol
Anhydrous THF (200 ml) was added to 2-bromo-2'-chloro-1,1'-biphenyl (20.0 g, 74.75 mmol) under a stream of nitrogen, stirred at -78 ° C, and n-BuLi (2.5M) was added thereto. in Hexane, 35.88 ml) was slowly added dropwise and reacted for 1 hour. Thereafter, the reacted mixture was added dropwise to a reactor with a mixture of phenyl(pyridin-3-yl)methanone (13.70 g, 74.75 mmol) (THF, 100 ml, -78 ° C), and stirred at room temperature for 2 hours. The reaction was terminated, extracted with dichloromethane, MgSO4 was added and filtered. After removal of the filtered organic layer solvent, the target compound was obtained by using column chromatography. GC-Mass(Theoretical value: 371.86 g / mol, Measured value: 371 g / mol).
(4'-chloro-[1,1'-biphenyl]-2-yl)(phenyl)(pyridin-3-yl)methanol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Anhydrous THF (200 ml) was added to <strong>[179526-95-5]2-bromo-4'-chloro-1,1'-biphenyl</strong> (20.0 g, 74.75 mmol) under a stream of nitrogen, stirred at -78 C, and n-BuLi (2.5M) was added thereto. in Hexane, 35.88 ml) was slowly added dropwise and reacted for 1 hour. Thereafter, the reacted mixture was added dropwise to a reactor with a mixture of phenyl (pyridin-3-yl) methanone (13.70 g, 74.75 mmol) (THF, 100 ml, -78 C), and stirred at room temperature for 2 hours. The reaction was terminated, extracted with dichloromethane, MgSO4 was added and filtered. After removal of the filtered organic layer solvent, the target compound was obtained by using column chromatography. GC-Mass(Theoretical value: 371.86 g / mol, Measured value: 371 g / mol).
With tert.-butylhydroperoxide; water; copper(II) sulfate In acetonitrile at 80℃; for 4h; Schlenk technique; Inert atmosphere;
78%
With tert.-butylhydroperoxide; copper(II) sulfate In acetonitrile at 90℃; for 4h;
5
In a clean and dry 10 ml round bottom flask, add 0.3 mmol of 3-ethynylpyridine,0.06 mmoles of copper sulfate, 0.6 mmoles of N-fluorobisbenzenesulfonamide,0.9 millimoles of tert-butyl hydroperoxide and 2 milliliters of acetonitrile,The reaction mixture was reacted at 90°C for 4 hours.After the reaction, the reaction mixture was extracted and concentrated,Then use petroleum ether and ethyl acetate as the eluent for column separation,43 mg of light yellow liquid was obtained, and the yield was about 78%.
(2-(methoxymethyl)phenyl)(phenyl)(pyridin-3-yl)methanol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Stage #1: 1-bromo-2-(methoxymethyl)benzene With iodine; magnesium In tetrahydrofuran at 60℃; for 2h; Inert atmosphere;
Stage #2: 3-Benzoylpyridine In tetrahydrofuran at 60℃; for 6.33333h;
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