Compound containing bipyrazole ring, intermediate thereof and application thereof
A technology of bispyrazole ring and compound is applied in the field of compounds containing bispyrazole ring, and can solve problems such as insufficient ligands
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Embodiment 1
[0195] The preparation of embodiment 1 intermediate a
[0196]
[0197] Add 1,3-diphenyl-propanedione 5g (0.023mol) and 20mL (4ml / g) N-methylpyrrolidone (NMP) into a 250mL four-neck round bottom flask, add bromine 4.30 at room temperature g (0.027mol, 1.2eq), the dropwise addition was completed in 5 minutes, and the yield was 97% (the yield was obtained by HPLC area normalization method, the same below). Directly raise the temperature to 45°C, add 6.43g (0.078mol, 3.5eq) of 3-methylpyrazole dropwise at this temperature, complete the dropwise addition in 5 minutes, keep warm for 12h, and the yield is 83%; without post-treatment, directly add 15mL ( 3mL / g) acetic acid, then add 30mL of methanol solution containing 3.6g (0.033mol, 1.5eq) phenylhydrazine (volume mass ratio of solution volume to 1,3-diphenyl-propanedione is 6ml / g), 10 The dropwise addition was completed within 1 minute, and the reaction was carried out at 45° C. for 12 hours, and the yield was 80%. Add water 2...
Embodiment 2
[0200] Add 1,3-diphenyl-propanedione 15g (0.067mol) and 60mL (4ml / g) N-methylpyrrolidone into a 250mL four-neck round bottom flask, add bromine 13.12g (0.082 mol, 1.22eq), the dropwise addition was completed in 20 minutes, and the yield was 98%. Directly raise the temperature to 45°C, add 19.28g (0.23mol, 3.5eq) of 3-methylpyrazole dropwise at this temperature, complete the dropwise addition in 10 minutes, keep warm for 18h, and the yield is 85%; without post-treatment, directly add 45mL ( 3mL / g) acetic acid, and then add 60mL (4ml / g) of methanol solution containing 10.86g (0.10mol, 1.5eq) phenylhydrazine, dropwise in 20 minutes, react at 45°C for 20h, yield 83%. After the reaction, add 80ml of water, precipitate the product from the solvent, filter, wash with 30mL of water, 15mL of methanol, and 15mL of n-heptane to obtain the crude product, which is 21.3g of a light yellow solid with a purity of 81% by high performance liquid chromatography. The crude product is dissolved in...
Embodiment 3
[0202]40g (0.178mol) of 1,3-diphenyl-propanedione and 120mL (3ml / g) of N-methylpyrrolidone were added to a 500mL four-neck round bottom flask, and bromine 32.50g (0.20 mol, 1.1eq), the dropwise addition was completed in 20 minutes, and the yield was 98%. Directly raise the temperature to 48°C, add 48.06g (0.0.58mol, 3.3eq) of 3-methylpyrazole dropwise at this temperature, complete the dropwise addition in 10 minutes, keep warm for 6-10h, and the yield is 86%; without post-treatment, directly , add 70mL (1.8mL / g) of acetic acid, then add 120mL (3ml / g) of methanol solution containing 25.18g (0.232mol, 1.3eq) of phenylhydrazine, add dropwise in 20 minutes, react at 40°C for 15h, the yield 83%. Add water 100mL after reaction finishes, product is separated out from solvent, filters, and 50mL washes with water, and 30mL methanol washes, and 20mL n-heptane washes, and obtains crude product HPLC purity 76% light yellow solid 56.9g, and crude product is dissolved in 80ml hot toluene (...
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