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With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 2h;
Example 1; Synthesis of cis-1-(2-fluoro-6-methylbenzoyl)-2-phenylpiperidine-3-carboxylic acid (3-trifluoromethylphenyl)amide; a) Pd(PPh3)4 (3.0 g, 2.6 mmol) was added to a solution of 2-chloro-3-carboxyethylpyridine (25 g, 134.7 mmol), phenylboronic acid (21.04 g, 172.6 mmol) and K2CO3 (55.1 g, 399 mmol) in 1,4-dioxane (200 mL) and water (200 mL). The reaction mixture was heated at 100 C. for 2 h. The solution was then cooled to room temperature and the dioxane was removed under reduced pressure. The resulting aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried (Na2SO4), filtered through celite, and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 10-100% EtOAc/hexanes) to get the 2-phenylpyridine derivative in 91% yield (27.98 g). LC-MS Rt (retention time): 2.45 min, MS: (ES) m/z 228 (M+H+).
5.27 g
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In toluene; for 4h;Reflux; Inert atmosphere;
A toluene solution (300 mL) of ethyl 2-chloronictinate (5.57 g), phenylboronic acid (4.76 g), tripotassium phosphate (8.91 g), 1,1'-bis (diphenylphosphino) ferrocene-palladiumdichloride dichloromethane complex (439 mg) was stirred under reflux for 4 hours in a nitrogen atmosphere. Water (100 mL) was added to the reaction solution, and the reaction solution was separated. The obtained organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified with silica gel column chromatography (hexane/ethyl acetate=96/4 to 75/25) to give ethyl 2-phenylnicotinate (5.27 g) as an oil. MS m/z 229 [M+H]
b) PtO2 (800 mg, 3.52 mmol) was added to a solution of <strong>[144501-28-0]2-phenyl-nicotinic acid ethyl ester</strong> (20 g, 88 mmol, prepared in step a above) in EtOH (60 mL) and concentrated HCl (15 mL). The reaction mixture was hydrogenated using a Parr shaker at 40-45 psi, for 1 h. The reaction mixture was then filtered through celite, washed with EtOH, and the filtrate was concentrated under reduced pressure. The residue was diluted with CH2Cl2 and washed with saturated NaHCO3. Purification by flash chromatography (SiO2, 0-20% MeOH/CH2Cl2) gave the desired product in 85% yield (17.4 g). LC-MS Rt (retention time): 1.73 min, MS: (ES) m/z 234 (M+H+).
With palladium on activated charcoal; hydrogen; In ethanol; acetic acid; at 20℃; under 3000.3 Torr; for 30h;
To an ethanol solution (30 mL) of <strong>[144501-28-0]ethyl 2-phenylnicotinate</strong> (3.41 g), palladium/carbon (1.30 g) and acetic acid (24 mL) were added, and the reaction mixture was stirred for 30 hours at room temperature under a medium pressure-hydrogen atmosphere (about 0.40 MPa). The mixture was filtered with Celite. Then the filtrate was concentrated under reduced pressure to give ethyl 2-phenylpiperidine-3-carboxylate as an oil.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 85℃; for 3h;Inert atmosphere;
General procedure: 10 mmol of 5-bromonicotinic acid ethyl ester, 12 mmol of phenylboronic acid,20 mmol of potassium carbonate, 0.5 mmol of tetrakis (triphenylphosphine) palladium was suspended in DME / H2O (40/10 mL)The reaction was carried out at 85 C for 3 hours after purging with nitrogen.After cooling, the filtrate was extracted with ethyl acetate and the ethyl acetate layer was washed three times with brine,Dried over anhydrous magnesium sulfate. Filtration, filtrate concentrated silica gel sample flash column chromatography (0-10% ethyl acetate / petroleum ether) to give 2.1 g of colorless oil.
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[ 144501-28-0 ]
1-(4-(3,5-dichloro-4-((2-phenylpyridin-3-yl)methoxy)phenyl)pyridin-2-yl)piperazine[ No CAS ]
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