Biphenyl multi-substituted 1,2,5,6-tetrahydropyridine compound and synthesis method and application thereof
A tetrahydropyridine compound technology, applied in the field of new biphenyl multi-substituted 1,2,5,6-tetrahydropyridine compounds and their synthesis, achieves the effect of low price, high purity and simple steps
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Embodiment 1
[0051] Add 1-(4-iodophenyl)-4-(4-iodophenylamino)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid to the 25ml reaction tube Ethyl ester (0.30g, 0.41mmol), phenylboronic acid (0.15g, 1.24mmol), (PdCl 2 (dppf)]CH 2 Cl 2 (6.70mg, 0.0082mmol) and sodium hydroxide (0.37g, 3.72mmol), after replacing the argon, add MeCN:H in addition to oxygen 2 O=3:1 mixed solvent 10ml. The mixture was stirred at 60°C for 5h, and TLC followed the reaction until the raw material was completely converted. After the reaction is completed, the reaction solvent is evaporated off, and the crude product is purified by column chromatography to obtain pure white powder 1-(biphenyl-4-yl)-4-(4-aminobiphenyl-4-yl)- 0.24 g of ethyl 2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate, with a yield of 90.3%.
[0052] 1 H-NMR (400MHz, DMSO) δ (ppm) = 10.30 (s, 1H), 7.60 (d, 2H, J = 7.2 Hz), 7.34 (m, 22H), 6.52 (t, 4H, J = 8.8 Hz) , 6.41 (s, 1H), 5.49 (s, 1H), 4.40 (m, 2H), 3.05 (m, 1H), 2.92 (m, 1H), 1.4...
Embodiment 2
[0055] Add 1-(4-bromophenyl)-4-(4-iodophenylamino)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid to the 25ml reaction tube Ethyl ester (0.26g, 0.41mmol), phenylboronic acid (0.30g, 2.48mmol), PdCl 2 (dppf) (12mg, 0.016mmol) and cesium carbonate (3.23g, 9.92mmol), after replacing the argon, add DMSO: H that removes oxygen 2 O=5:1 mixed solvent 6ml. The mixture was stirred at 110°C for 9 h, and TLC followed the reaction until the raw material was completely converted. After the reaction is completed, cool to room temperature, transfer the reaction solution to a separatory funnel, add 20 ml of distilled water and 15 ml of ethyl acetate, extract, separate the lower aqueous phase, and repeat 6 times. The organic phase was dried with anhydrous sodium sulfate, and the organic phase was removed by rotary evaporation. The crude product was purified by column chromatography to obtain pure white powder 1-(biphenyl-4-yl)-4-(4-aminobiphenyl- 0.22 g of ethyl 4-yl)-2,6-diphenyl-1...
Embodiment 3
[0059] Add 1-(4-iodophenyl)-4-(4-iodophenylamino)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid to the 25ml reaction tube Ethyl ester (0.50g, 0.79mmol), p-toluene boronic acid (0.54g, 3.95mmol), (PdCl 2 (dppf)] (26mg, 0.036mmol) and potassium carbonate (1.91g, 13.81mmol), after replacing the argon, add DMF: H to remove oxygen 2 O=4:1 mixed solvent 8ml. The mixture was stirred at 80°C for 4 h, and TLC followed the reaction until the raw material was completely converted. After the reaction is completed, cool to room temperature, transfer the reaction solution to a separatory funnel, add 25ml of distilled water, 20ml of ethyl acetate, extract, separate the lower aqueous phase, and repeat 6 times. The organic phase was dried with anhydrous sodium sulfate. After the organic phase was evaporated by rotary evaporation, the crude product was purified by column chromatography to obtain pure 1-(4'-methylbiphenyl-4-yl)-4-( 4'-methyl-4-aminobiphenyl-4-yl)-2,6-diphenyl-1,2,5,6...
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