- Novel synthesis method of N-Boc-1,2,5,6-tetrahydropyridine-4-boric acid pinacol ester
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The invention discloses a novel synthesis method of N-Boc-1,2,5,6-tetrahydropyridine-4-boric acid pinacol ester. The synthesis method comprises following three steps: taking 4-bromopyridine hydrochloride as the primary raw material, reacting 4-bromopyridine hydrochloride with tert-butyl chloroformate or di-tert-butyl bicarbonate to prepare 4-bromo-N-Boc-pyridine chloride; reducing 4-bromo-N-Boc-pyridine chloride by NaBH4 to prepare N-Boc piperidine-4-vinyl bromide; and finally, carrying out coupling reactions between N-Boc piperidine-4-vinyl bromide and bis(pinacolato) diboron to prepare the target product: N-Boc-1,2,5,6-tetrahydropyridine-4-boric acid pinacol ester. The synthesis route has the advantages of easily available raw materials, mild conditions, few byproducts, and high yield, and is suitable for industrial enlarged production.
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Paragraph 0005; 0006; 0007
(2019/10/02)
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- New synthesis method of N-substituted-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester
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The invention discloses a new synthesis method of N-substituted-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester. The new synthesis method of the N-substituted-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester comprises the following three reaction steps: firstly, performing reaction on 4-bromopyridine hydrochloride and clR1 to prepare 4-bromine-N-substituted-pyridine chloride; then preparing N-substituted-piperidine-4-alkenyl bromide through NaBH4 reduction; finally, preparing the target product N-substituted-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester through a Grignard method and methoxy boric acid ester. The synthesis route has the advantages of high universality, cheap and easily available raw materials, mild reaction condition, few byproducts, high yield andthe like, and the product has high economic property and strong market competitiveness and is suitable for industrialized production. The formula is as shown in the description, wherein R1=-Boc;-Cbz;-Bz;-Bn;-Fmoc;-Me;-Et;-iPr;-Ph.
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Paragraph 0022-0023; 0025
(2019/12/25)
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- Nitrogen aryl benzothiazole PARP inhibitors, preparation methods and uses thereof
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The present invention discloses a class of novel PARP inhibitor compounds represented by the following general formula I and having a nitrogen aryl benzothiazole structure, stereoisomers, preparation methods and intermediates thereof, and applications of the novel PARP inhibitor compounds in preparation of drugs for prevention and treatment of PARP (poly ADP-ribose-ribose polymerase) related diseases. Compared to the similar drugs in the prior art, the compounds of the preset invention hava advantages of long in vivo action time, long half life, and significantly improved bioavailability. The general formula I is defined in the specification.
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Paragraph 0201; 0202; 0203; 0204; 0205
(2016/10/07)
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- Synthesis method of N-substituted-1,2,5,6-tetrahydropyridine-4-borate
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The invention discloses a synthesis method of N-substituted-1,2,5,6-tetrahydropyridine-4-borate. According to the synthesis method, N-substituted-4-piperidone is taken as the raw material, N-substituted-4-piperidone, triaryl phosphite, halogen, and organic alkali carry out reactions, the carbonyl group is converted into vinyl halogen, and finally the reaction product reacts with isopropyl magnesium chloride-lithium chloride and alkoxyl borate to generate N-substituted-1,2,5,6-tetrahydropyridine-4-borate. The synthesis method has the advantages that the raw materials are easily available, the operation is simple and convenient, the product purity is high, the ultralow temperature condition and palladium catalytic coupling are not needed, the cost is reduced, the route is optimized, and thus the product is competitive in the market.
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Paragraph 0019
(2016/11/17)
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- Synthesis method of N-substituted piperidine-4-borate
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The invention discloses a synthesis method of N-substituted piperidine-4-borate. According to the synthesis method, N-substituted-4-piperidone is taken as the raw material, N-substituted-4-piperidone, triaryl phosphite, halogen, and organic alkali carry out reactions, the carbonyl group is converted into vinyl halogen, then the reaction product reacts with metal lithium and bis(diisopropylamine)boron halide, then dihydric alcohol is added, finally the reaction product is hydrogenated in the presence of palladium-charcoal so as to obtain N-substituted piperidine-4-borate, and the product purity is 98% or more. The synthesis method has the advantages that the raw materials are easily available, the operation is simple and convenient, the product purity is high, the cost is reduced, the route is optimized, and thus the core competitiveness of the product is increased.
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Paragraph 0019
(2016/10/09)
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- Ruthenium-catalyzed transformation of alkenyl triflates to alkenyl halides
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In the presence of a ruthenium catalyst, alkenyl triflates were found to be transformed to the corresponding bromides, chlorides and iodides simply by treatment with a lithium halide (1.2 equiv.). The Royal Society of Chemistry 2009.
- Shirakawa, Eiji,Imazaki, Yusuke,Hayashi, Tamio
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supporting information; experimental part
p. 5088 - 5090
(2009/12/08)
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