Non-transition metal-catalyzed 2-phenylpyridine compound synthesis method
A technology of phenylpyridine and metal catalysis is applied in the field of preparation of pharmaceutical and chemical intermediates, and achieves the effects of large use value, social and economic benefits, readily available raw materials, and simple steps.
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Embodiment 1
[0037] Embodiment 1: Synthesis of 2-phenylpyridine (2a)
[0038]
[0039] Weigh pyridine-2-carboxylic acid (36.9mg, 0.3mmol), potassium carbonate (20.8mg, 0.15mmol), and add benzene (3mL) and tert-butyl hypochlorite (102μL, 0.9mmol) to 25mL of Schlenk reaction bottle, and then placed in a 60°C oil bath for 20h. After the reaction, the solvent was removed under reduced pressure, and petroleum ether / ethyl acetate was used as the eluent, and the silica gel column was used for separation. The yield of 2-phenyl pyridine was 86%. 1 HNMR (400MHz, CDCl 3 ):δ8.70(dt,J=4.8,1.4Hz,1H),8.03-7.96(m,2H),7.77-7.69(m,2H),7.51-7.45(m,2H),7.45-7.38(m ,1H),7.25-7.16(m, 1 H); 13 CNMR (100MHz, CDCl 3 ): δ157.5, 149.7, 139.4, 136.8, 128.9, 128.7, 126.9, 122.1, 120.6.
Embodiment 2
[0040] Embodiment 2: Synthesis of 4-Chloro-2-phenylpyridine (2b)
[0041]
[0042] Weigh 4-chloropyridine-2-carboxylic acid (36.9mg, 0.3mmol), potassium carbonate (41.6mg, 0.3mmol), and add benzene (5mL) and tert-butyl hypochlorite (34μL, 0.3mmol) to 25mL in sequence in a Schlenk reaction flask, and then placed in an oil bath at 40°C for 15 h. After the reaction, the solvent was removed under reduced pressure, and petroleum ether / ethyl acetate was used as the eluent, and the silica gel column was used for separation. The yield of 4-Chloro-2-phenylpyridine was 75%. 1 H NMR (400MHz, CDCl 3 ):δ=8.57(d,J=5.3Hz,1H),7.96(dt,J=8.4,2.1Hz,2H),7.72(d,J=1.9Hz,1H),7.48-7.43(m,3H) ,7.23(dd,J=5.3,1.9Hz,1H); 13 C NMR (100MHz, CDCl 3 ): δ159.0, 150.5, 144.8, 138.1, 129.6, 128.9, 127.0, 122.3, 120.9.
Embodiment 3
[0043] Embodiment 3: Synthesis of 3-methyl-2-phenylpyridine (2c)
[0044]
[0045] Weigh 3-picoline-2-carboxylic acid (36.9mg, 0.3mmol), potassium phosphate (127.4mg, 0.6mmol), and add benzene (1mL) and tert-butyl hypochlorite (68μL, 0.6mmol) to 25mL Schlenk reaction flask, and then placed in an 80°C oil bath to react for 8h. After the reaction, the solvent was removed under reduced pressure, and petroleum ether / ethyl acetate was used as the eluent, and silica gel column separation was performed. The yield of 3-methyl-2-phenylpyridine was 71%. 1 H NMR (400MHz, CDCl 3):δ8.53(dd,J=4.7,1.1Hz,1H),7.57(dd,J=7.7,0.9Hz,1H),7.53-7.49(m,2H),7.47-7.34(m,3H), 7.17(dd,J=7.7,4.8Hz,1H),2.34(s,3H); 13 C NMR (100MHz, CDCl 3 ): δ158.7, 147.0, 140.6, 138.5, 130.8, 128.9, 128.1, 127.9, 122.1, 20.0.
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