* 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.
With iron; ammonium chloride; In ethanol; water; at 70 - 80℃; for 1.0h;
General procedure: Ethanol (20 ml) and water (5 ml) was mixed, added with iron powder, and heated to 70-80C. Ammonium chloride (0.1 g, 2.1 mmol) was added, followed by 2-phenyl-5-nitropyridine (2.0 g, 10.0 mmol) obtained in (i). The reaction was carried out at 70-80C for 1 hour. After the completion of the reaction, the iron powder was filtered while hot through Celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in isopropyl alcohol, crystallized and filtered with addition of water to give the title compound (1.4 g, 81.9%).
With iron; ammonium chloride; In ethanol; water; at 70 - 80℃; for 1.0h;
General procedure: Ethanol (20 ml) and water (5 ml) was mixed, added with iron powder, and heated to 70-80C. Ammonium chloride (0.1 g, 2.1 mmol) was added, followed by 2-phenyl-5-nitropyridine (2.0 g, 10.0 mmol) obtained in (i). The reaction was carried out at 70-80C for 1 hour. After the completion of the reaction, the iron powder was filtered while hot through Celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in isopropyl alcohol, crystallized and filtered with addition of water to give the title compound (1.4 g, 81.9%).
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water;Inert atmosphere; Reflux;
General procedure: To 0.329 g (1.5 mmol) 4-iodoaniline, 1.8 mmol ArB(OH)2, 0.318 g (3 mmol) Na2CO3 and 75 mg (0.075 mmol) PdCl2(PPh3)2, 15 mL of a blended solution of dioxane and water (v/v = 3/1) was added under N2 atmosphere. Then the reaction was heated to reflux and monitored by TLC. Upon cooling, the reaction mixture was dilute with sat. NH4Cl solution, then extracted with EA (3×20 mL), and the organic layer was washed with saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography to afford different 4-aminobiphenyl derivatives. According to the reductive amination procedure, the 4-aminobiphenyl derivative was further treated with salicylaldehyde and to afford the corresponding compound 5&6.
2-(((6-(4-methoxyphenyl)pyridin-3-yl)amino)methyl)phenol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
General procedure: Under an atmosphere of N2, 0.175 g (1 mmol) compd. 2 was dissolved in methanol, 0.11 mL (1.05 mmol) salicylaldehyde was added and stirred overnight at room temperature. When compd. 2 disappeared, NaBH4 (61 mg, 1.6 mmol) was added. After stirring for 10 min, the reaction was quenched by sat. NH4Cl solution, then extracted with CH2Cl2 (3×20 mL), and the organic layer was washed with saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography (PE:EtOAc = 15:1) to afford 0.230 g (82%) E6 as white solid.
(2-chloro-9-cyclopentyl-9H-purin-6-yl)-[6-(4-methoxyphenyl)pyridin-3-yl]amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
84%
With N-ethyl-N,N-diisopropylamine; In propan-1-ol; at 100℃;Sealed tube;
To a suspension of 9-substituted-2,6-dichloro-9H-purine (8)(2.00 mmol) in a mixture of n-propanol (10 mL) and N,N-diisopropyl-N-ethylamine (6.00 mmol), appropriate amine (2.05 mmol)was added. The suspension was heated while stirring in a sealedtube under an argon atmosphere at 100 C for 2-6 h. The reactionwas checked by TLC using mobile phase toluene-ethylacetate (1:1,v/v). After the completion of the reaction, the reaction mixture wascooled to room temperature and evaporated under reduced pressure.The residue was partitioned between water (50 mL) and dichloromethane (50 mL), and the water phase was extracted twoadditional times with the same volume of dichloromethane. Thecombined organic phases were washed with water and brine andevaporated under reduced pressure. The crude product was crystallizedfrom petroleum ether/ethylacetate (3:1).
With 5%-palladium/activated carbon; hydrogen; In methanol; under 760.051 Torr;
General procedure: The crude nitroderivative (5) from the previous step(0.75 mmol) was hydrogenated under atmospheric pressure inmethanol (50 mL) with 5% wt. palladium on charcoal (50 mg). Afterthe consumption of hydrogen, the reaction mixture was filteredthrough Celite, washed with methanol and evaporated underreduced pressure. The crude product was dissolved in 2M hydrochloricacid (50 mL) and extracted with dichloromethane (25 mL).The water phase was neutralized with 5% sodium hydrogen carbonate,and the precipitate was filtered off and washed with water.The crude product was dried in a vacuum desiccator and finallypurified by flash column chromatography using mobile phasechloroform/methanol (4:1, v/v).
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