A kind of oxadiazole derivative and its application
A Derivative, Oxadiazole Technology
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[0042] In the second embodiment of the present invention, the present invention provides a method for preparing the above-mentioned oxadiazole derivatives, the method comprising:
[0043] S1: Put 2-pyridinecarboxylic acid and excess ethanol in a two-necked flask, add concentrated sulfuric acid drop by drop under the condition of 50°C, the metering ratio of the concentrated sulfuric acid to the 2-pyridinecarboxylic acid is 1:1, Immediately after the dropwise addition, the temperature was raised to 80°C, and the reaction was carried out for 12 hours to obtain ethyl 2-pyridinecarboxylate;
[0044] S2: Put the obtained ethyl 2-pyridinecarboxylate and excess hydrazine hydrate into a reaction flask, and react under the protection of argon at 80°C for 15 hours to obtain 2-pyridinecarboxyhydrazide;
[0045] S3: Using anhydrous tetrahydrofuran as a solvent, mix the obtained 2-picolylhydrazide and m-bromobenzoyl chloride at a ratio of 1:1, and react under argon protection under the acti...
Embodiment 1
[0061] Embodiment 1: the preparation of intermediate A and intermediate B
[0062]
[0063] Weigh 8.61g (about 0.07mol) of 2-pyridinecarboxylic acid, 120ml of absolute ethanol in a two-necked flask, take 3.8ml of concentrated sulfuric acid in a dropping funnel, and add it dropwise to the reaction flask at 50°C; Immediately after the addition, the temperature was raised to 80° C., and the reaction was carried out for 12 hours. After cooling, the mixture was purified by column chromatography to obtain ethyl 2-picolinate as a yellow transparent liquid.
[0064]
[0065] Weigh 8.6 g (about 0.06 mol) of ethyl 2-picolinate and 20 ml of 80% hydrazine hydrate, heat and react at 80° C. under argon for 15 hours to obtain 2-picolinic acid hydrazide. The yield is about 85%.
[0066]
[0067] Weigh 2-pyridinecarbohydrazide (4.23g, 30mmol), 3-bromobenzoyl chloride (6.77g, 30mmol), and anhydrous sodium carbonate (1.64g, 15mmol) into a reaction flask, using anhydrous tetrahydrofuran...
Embodiment 2
[0074] Embodiment 2: Preparation of M1
[0075]
[0076] Weigh 1.1g (3.6mmol) of intermediate A and 1.03g (3.6mmol) of 3-(9-carbazolyl)phenylboronic acid in a two-necked flask, then add 4ml of absolute ethanol and 5ml of 2mol / L aqueous sodium carbonate , 20ml of toluene, and then added 125mg of tetrakis(triphenylphosphine)palladium (0.108mmol). Under the protection of argon, react at 80°C for 12 hours. The crude product was purified by column chromatography to obtain white solid M11.3g (yield 77%). TOF MS(m / z):464.1644[M] + .
[0077] 1 H NMR (500MHz, CDCl 3 )δ: 8.79(d, J=7.5Hz, 1H), 8.48(s, 1H), 8.30(d, J=8.0Hz, 1H), 8.22(d, J=7.5Hz, 1H), 8.15(d, J=7.5Hz, 2H), 7.87(m, 2H), 7.81(d, J=7.5Hz, 1H), 7.77(d, J=8.0Hz, 1H), 7.71(t, J=7.8Hz, 1H) , 7.60 (m, 2H), 7.47 (s, 1H), 7.45 (s, 2H), 7.43-7.40 (m, 2H), 7.29 (t, J=7.8Hz, 2H).
[0078] 13 C NMR (126MHz, CDCl 3 )δ165.38,163.95,150.25,143.54,141.76,141.22,140.87,138.46,137.23,130.69,130.48,129.75,126.60,126.33,126.04,125...
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