* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
1-(4-propylphenyl)-2-(2-ethoxy-pyridine-5-yl)-acetylene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
EXAMPLE 2 0.05 m of ethylmagnesium bromide in ether are added to a mixture of 0.05 m of 4-propylphenylacetylene at 0-10. The mixture is stirred for 4 hours at room temperature and then a solution of 0.05 m of <strong>[55849-30-4]2-ethoxy-5-bromopyridine</strong> and 0.5 g of NiCl2 (Ph3 P)2 in ether is added. After stirring for 6 hours at room temperature and customary work-up 1-(4-propylphenyl)-2-(2-ethoxy-pyridine-5-yl)-acetylene is obtained.
With ferric(III) bromide; 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 10℃; for 12h; Inert atmosphere; Sealed vessel; stereoselective reaction;
General procedure for products 3h-3n
General procedure: FeBr3 (0.5 mmol) and DDQ (0.6 mmol) were placed in a Schlenk tube. To this 2 mL chlorobenzene, diphenylmethane (1a) (0.5 mmol) was then added and phenylacetylene (2a) (0.6 mmol) was dropped into the system through dropping funnel. The tube was sealed and flushed with nitrogen, then the contents were stirred for 12 h at 10 °C. The reaction mixture was flushed through a short column of silica gel with dichloromethane, then the solvent was removed under vacuum. The product was isolated from the dark purple crude mixture by column chromatography (petroleum ether: THF = 20: 1).
bis(acetonitrile)palladium(II) dichloride[ No CAS ]
4-Chloro-2-cyclohexyl-1-p-tolylethynylbenzene[ No CAS ]
[ 534-17-8 ]
[ 62452-73-7 ]
[ 564483-18-7 ]
2-Cyclohexyl-4-(4-hexylbenzeneethynyl)-1-(4-propyl-benzeneethynyl)benzene[ No CAS ]
2-Cyclohexyl-4-(4-hexylphenylethynyl)-1-(4-propylphenylethynyl)-benzene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In 1,4-dioxane; water;
3.5) 2-Cyclohexyl-4-(4-hexylphenylethynyl)-1-(4-propylphenylethynyl)-benzene 6 4.5 g (11.87 mmol) of 10, 1.7 g (11.87 mmol) of 1-n-propyl-4-ethynyl-benzene, 8.5 g (26.12 mmol) of caesium carbonate, 30 mg (0.1 mmol) of bis(acetonitrile)palladium(II) chloride and 170 mg (0.35 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl are dissolved in 35 ml of dioxane under nitrogen and heated at 100 C. overnight. 100 ml of water are added to the cooled solution, and the mixture is extracted twice with methyl t-butyl ether (100 ml). The combined organic phases are washed with water, dried over sodium sulfate and evaporated in vacuo. The residue is purified by column chromatography, giving the title compound 6 as a solid. Delta? -0.6 Deltan 0.294 gamma1 5884 mPa·s
bis(triphenylphosphine)palladium(II) dichloride[ No CAS ]
[ 63279-58-3 ]
[ 62452-73-7 ]
[ 1296203-34-3 ]
Yield
Reaction Conditions
Operation in experiment
copper(I) iodide; In n-heptane; water; triethylamine;
Synthesis Example 21-Bromo-4-(4-n-propylphenylethynyl)naphthalene15.3 g (43.6 mmol) of 1-iodo-4-bromonaphthalene and 7.25 g (5.3 mmol) of 4-n-propylphenylacetylene are initially introduced in 200 ml of NEt3, 170 mg (0.9 mmol) of copper(I) iodide and 600 mg (0.9 mmol) of bis-(triphenylphosphine)palladium(II) chloride are added, and the mixture is refluxed for 30 minutes.The batch is cooled, water and heptane are added, and the phases are separated.The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated in a rotary evaporator.The residue is purified by column chromatography (SiO2, heptane), and the further purification is carried out by recrystallisation from isopropanol.
With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; for 0.5h;Reflux;
15.3 g (43.6 mmol) of 1-iodo-4-bromonaphthalene and 7.25 g (5.3 mmol) of 4-n-propylphenylacetylene are initially introduced in 200 ml of NEt3, 170 mg (0.9 mmol) of copper(I) iodide and 600 mg (0.9 mmol) of bis-(triphenylphosphine)palladium(II) chloride are added, and the mixture is refluxed for 30 minutes. The batch is cooled, water and heptane are added, and the phases are separated. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated in a rotary evaporator. The residue is purified by column chromatography (SiO2, heptane), and the further purification is carried out by recrystallisation from isopropanol.
With indium(III) triflate; water; toluene-4-sulfonic acid; In 1,2-dichloro-ethane; for 4h;Sealed tube; Reflux;
General procedure: The reaction mixture of In(OTf)3 (11.2 mg, 2 mol %), PTSA (57.1 mg, 30 mol %), DCE (2.0 mL), alkynes 1a-1n or 1p-1t (1.0 mmol) and water (0.2 mL) in a 10 mL flask or in a 10 mL sealed tube was stirred at reflux and monitored periodically by TLC. Upon completion, DCE was removed under reduced pressure using an aspirator, and then the residue was purified by flash chromatography (PE/EA) on silica gel to afford corresponding carbonyl compounds 2a-2n or 2p-2t.
91%
With C20H14AuN2O2(1+)*Cl(1-); water; trifluoroacetic acid; In methanol; at 80℃; for 5h;Sealed tube;
General procedure: Alkyne (0.5 mmol), catalyst (2.0 mol%), H2O (4.0 equiv., 0.04 mL) and CF3COOH (2.0 mol%) were dissolvedin MeOH (0.4 mL) and the homogeneous solution was stirred in a sealed tube at 80C for 5 h. After the completion of the reaction, the mixture was cooled to room temperature, and then CH2Cl2 and H2O were added to it. The organic layer was separated and washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified over silica gel by column chromatography (25% EtOAc in hexane).
89%
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); water; In methanol; at 110℃; for 6h;
The catalyst [(IPr) AuCl] (3.1mg, 0.5mol%), 4- propylbenzene acetylene (1mmol), in methanol (1ml) and water (0.5ml) was added successively 25ml reactor.After the reaction mixture was reacted for 6 hours at 110 , cooled to room temperature.Rotary evaporation to remove the solvent, then purified by column chromatography (eluent: petroleum ether / ethyl acetate) to give pure title compound, yield: 89%
88%
With Perfluorooctanesulfonic acid; C8AgF17O3S*H2O; In water; at 100℃; for 8h;Darkness;
General procedure: To the mixture of phenylacetylene (1 mmol), water (3.0 mL),silver perfluorooctanesulfonate (5 mol%) and perfluorooctane sulfonateacid (2 mol%) was added. The mixture was stirred at 100 Cfor 8 h. The solution was extracted with n-hexane (diethyl ether)(3 5 mL), the combined extract was dried with anhydrous MgSO4. The rest of the solution was used for the next cycle of reaction. Theextraction solvent was removed and the crude product was separatedby column chromatography to give the pure sample.
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); water; silver trifluoromethanesulfonate; In methanol; at 120℃; for 6h;
The 4-propylphenylacetylene (144 mg, 1.0 mmol), cat. [Au] (6 mg, 1 µM %), AgOTf (2.6 mg, 1 µM %), water (36 mg, 2 mmol) and methanol (1 ml) are added to the 25 mL of Claisen tube or. After closing the reaction at 120 C for 6 hours, cooling to room temperature. Then adding formic acid amine (315 mg, 5 mmol) and cat. [Rh] (6.2 mg, 1 mmol %), the reaction mixture in oil bath heated to 80 C, reaction 12 hours, cooling to room temperature. Rotary evaporation of the solvent and add a certain amount of ethyl acetate and water extraction, the organic phase of the resulting product after concentrated hydrochloric acid the reflex process, rotary evaporation to remove the solvent, the final petroleum ether washing and filtering to obtain the pure target compound, yield: 85%
With copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 72h; Inert atmosphere;
2
Pt(PPh3)2Cl2 (360 mg, 0.54 mmol) and CuI (10.0 g, 0.053 mmol) were dissolved in 6 mL triethylamine and 18 mL THF, then argon was bubbled through the solution for 20 min. 4-propyl-phenylacetylene (185 mg, 1.30 mmol) was added dropwise and the resulted solution was stirred for 3 days at room temperature. After the reaction was completed, the solution was filtrated and the solvent was removed under reduced pressure. The crude produce was purified by flash chromatography with petroleum ether/dichloromethane (1:1) as the eluant. The product was collected as yellow solid (180 mg, 37.5 %).
With copper(l) iodide; triethylamine at 20℃; for 72h; Inert atmosphere;
2
General procedure: Pt(PPh3)2Cl2 (360 mg, 0.54 mmol) and CuI (10.0 g, 0.053 mmol) were dissolved in 6 mL triethylamine and 18 mL THF, then argon was bubbled through the solution for 20 min. 4-propyl-phenylacetylene (185 mg, 1.30 mmol) was added dropwise and the resulted solution was stirred for 3 days at room temperature. After the reaction was completed, the solution was filtrated and the solvent was removed under reduced pressure. The crude produce was purified by flash chromatography with petroleum ether/dichloromethane (1:1) as the eluant. The product was collected as yellow solid (180 mg, 37.5 %).
2,3,5,6-tetrafluoro-4-(4-(4-propylphenyl)-1H-1,2,3-triazol-1-yl)benzonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
85%
With sodium azide; copper(II) acetate monohydrate In acetonitrile at 20℃; for 8h; Schlenk technique;
General procedure for thesynthesis of the products (sodium azide, phenylacetyleneand pentafluorobenzonitrile as the example)
General procedure: Sodium azide (13.0 mg, 0.20mmol) and Cu(OAc)2.H2O (4.0 mg, 10 mol %) were weighed to a Schlenk tube, and CH3CN(0.5 mL) was added. Then pentafluorobenzonitrile (42.5 mg, 0.22 mmol) and phenylacetylene (30.6 mg, 0.30mmol) were added to the tube, respectively. The mixture was stirred at roomtemperature for 8 h until it was completed (by TLC). Water (5.0 mL) was addedand the mixture was extracted with ethyl acetate (3×10.0 mL). The organicextracts were combined, dried with anhydrous magnesium sulfate and thenconcentrated in vacuo. The residue was purified on silica gel to afford the product 3a
With copper(II) acetate hydrate; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 0.5h; Schlenk technique; Inert atmosphere;
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; tetrabutyl-ammonium chloride; benzoic acid anhydride; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃; for 16h; Irradiation; regioselective reaction;
With copper(II) nitrate trihydrate; iodine In dimethyl sulfoxide at 60℃; for 5h; Sealed tube;
II. General procedure for synthesis of 3 (3ac as an example)
General procedure: The mixture of phenylacetylene 1a (1.0 mmol), 2-amino-4-methylpentanoic 2c (1.0 mmol) was mixedwith Cu(NO3)2•3H2O (0.5 mmol), and I2(1.0 mmol). The mixture was heated at 60 °C in 4 mL of DMSO in asealed vessel for 5 h till almost completed conversion of the substrates monitored by TLC analysis. Then 50mL water was added to the mixture, which was extracted with EtOAc three times (3 × 50 mL). The extractwas washed with Na2S2O3 solution, dried over anhydrous Na2SO4 then the solvent was removed underreduced pressure. The crude product was purified by column chromatography on silica gel (eluent:petroleum ether/EtOAc = 50/1) to afford the product 3ac
6-hydroxy-6-((4-propylphenyl)ethynyl)indolo[2,1-b]quinazolin-12(6H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
73%
With copper(II) choride dihydrate; potassium carbonate In 1,4-dioxane at 60℃; for 36h; Schlenk technique;
Copper-Catalyzed Addition Reaction of Tryptanthrins andAlkynes - General Procedure
General procedure: In air, a clean and dried Schlenk tube was charged with CuCl2·2H2O (0.02 mmol,10 mol%), K2CO3 (0.4 mmol, 2.0 equiv.),tryptanthrin 1a (0.2 mmol, 1.0 equiv.), alkyne 2 (1.0 mmol, 5.0 equiv.), and 1,4-dioxane or THF (2 mL). The resulting mixture was stirred at the 60 °C or 80 °C for 36 h until the reaction completed. The crude mixture was purified through flash column chromatography on a silica gel using DCM/EtOAc (100:1, v/v) as eluent to give the desired products.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
