Compounding method for alpha-aryl- alpha-(5-pyridyl) acetate derivative
A synthesis method and derivative technology, applied in organic chemistry and other directions, can solve problems such as difficult activation, and achieve the effects of easy product, product purification, and simple steps.
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Embodiment 1
[0037] The synthetic method of α-aryl-α-(5-pyridyl) acetate derivative, comprises the following steps:
[0038] (1) In a sealed tube, add 2-pyrrolidinopyridine (29.6mg, 0.2mmol), methyl phenyldiazoacetate (105.6mg, 0.3mmol), cobalt bromide (2.2mg, 5%mmol), Copper acetate (3.6mg, 10%mmol), trifluoroethanol (2mL), and the mixture was stirred at 60°C for 12h. After the reaction was completed, the reaction system was cooled to room temperature, filtered, spin-dried, and further separated and purified by column chromatography to obtain 46.7 mg of the product with a yield of 79%.
[0039] The structural characterization data of the product obtained in this embodiment are as follows:
[0040] 1 H NMR (400MHz, CDCl 3 )δ8.08(s,1H),7.45(d,J=8.5Hz,1H),7.35–7.24(m,5H),6.34(d,J=8.8Hz,1H),4.90(s,1H), 3.74(s,3H), 3.50–3.40(m,4H), 2.04–1.95(m,4H). See the hydrogen spectrum figure 1 .
[0041] 13 C NMR (101MHz, CDCl 3 )δ173.2, 156.6, 147.9, 138.9, 137.3, 128.6, 128.2, 127.2, 121.2, 106...
Embodiment 2
[0046] The synthetic method of α-aryl-α-(5-pyridyl) acetate derivative, comprises the following steps:
[0047] (1) In a sealed tube, add 2-indolinylpyridine (39.2mg, 0.2mmol), methyl phenyldiazoacetate (70.4mg, 0.4mmol), cobalt bromide (2.2mg, 5%mmol) , copper acetate (3.6mg, 10%mmol), trifluoroethanol (2mL), and the mixture was stirred at 80°C for 12h. After the reaction was completed, the reaction system was cooled to room temperature, filtered, spin-dried, and further separated and purified by column chromatography to obtain 30.3 mg of the product with a yield of 44%.
[0048] The structural characterization data of the product obtained in this embodiment are as follows:
[0049] 1 H NMR (400MHz, CDCl 3 )δ8.36(d, J=4.2Hz, 1H), 8.17(d, J=8.2Hz, 1H), 7.59(t, J=7.8Hz, 1H), 7.36(d, J=3.1Hz, 4H) ,7.32–7.26(m,2H),7.20–7.15(m,1H),6.78(t,J=8.2Hz,2H),5.03(s,1H),4.05(t,J=8.5Hz,2H), 3.78(s, 3H), 3.20(t, J=8.5Hz, 2H). See the hydrogen spectrum image 3 .
[0050] 13 C NMR (101...
Embodiment 3
[0055] The synthetic method of α-aryl-α-(5-pyridyl) acetate derivative, comprises the following steps:
[0056] (1) In a sealed tube, add 4-methyl-2-pyrrolidinylpyridine (32.4mg, 0.2mmol), methyl phenyldiazoacetate (123.2mg, 0.7mmol), cobalt bromide (2.2mg, 5%mmol), copper acetate (3.6mg, 10%mmol), trifluoroethanol (2mL), and the mixture was stirred at 90°C for 12h. After the reaction was completed, the reaction system was cooled to room temperature, filtered, spin-dried, and further separated and purified by column chromatography to obtain 38.4 mg of the product with a yield of 62%.
[0057] The structural characterization data of the product obtained in this embodiment are as follows:
[0058] 1 H NMR (400MHz, CDCl 3 )δ7.85(s,1H),7.25–7.13(m,5H),6.10(s,1H),4.96(s,1H),3.65(s,3H),3.40–3.31(m,4H),2.07 (s,3H), 1.94–1.87(m,4H). See the hydrogen spectrum Figure 5 .
[0059] 13 C NMR (100MHz, CDCl 3 )δ173.2, 156.7, 147.6, 146.5, 138.0, 128.8, 128.5, 127.2, 120.8, 107.7, 52...
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