159503-91-0

Basic information

• Product Name: tert-butyl 4-broMo-5,6-dihydropyridine-1(2H)-carboxylate
• Synonyms: tert-butyl 4-broMo-5,6-dihydropyridine-1(2H)-carboxylate
• CAS NO: 159503-91-0
• Molecular Formula: C₁₀H₁₆BrNO₂
• Molecular Weight: 262.14354
• EINECS: -0
• Mol File: 159503-91-0.mol

Chemical Properties

• Boiling Point: 299.6±40.0 °C(Predicted)
• Appearance: /
• Density: 1.377±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -2.90±0.40(Predicted)
• CAS DataBase Reference: tert-butyl 4-broMo-5,6-dihydropyridine-1(2H)-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 4-broMo-5,6-dihydropyridine-1(2H)-carboxylate(159503-91-0)
• EPA Substance Registry System: tert-butyl 4-broMo-5,6-dihydropyridine-1(2H)-carboxylate(159503-91-0)

Safety Data

• Hazardous Substances Data: 159503-91-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Tert-butyl 4-bromo-5,6-dihydropyridine-1(2H)-carboxylate is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, tert-butyl 4-bromo-5,6-dihydropyridine-1(2H)-carboxylate is utilized as a versatile building block for the creation of a wide range of chemical products, taking advantage of its reactivity and functional group compatibility.
Used in the Production of Biologically Active Compounds:
Tert-butyl 4-bromo-5,6-dihydropyridine-1(2H)-carboxylate is employed as a precursor in the synthesis of biologically active compounds, leveraging its unique structure to enhance the properties and effectiveness of these compounds in various applications.

Upstream product

• 138647-49-1 4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 24608-52-4 tert-butyl chloroformate 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 589-87-7 1,4-bromoiodobenzene 
• 375853-82-0 tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate 

Downstream Products

• 1167991-21-0 N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid neopentyl glycol ester 
• 375853-82-0 tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate 
• 1240969-31-6 4-(4-ethoxycarbonylphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 741729-98-6 ethyl 4-(piperidin-4-yl)benzoate 
• 206446-48-2 tert-butyl 4-[4-(ethoxycarbonyl)phenyl]piperidine-1-carboxylate 

Relevant articles and documents

Novel synthesis method of N-Boc-1,2,5,6-tetrahydropyridine-4-boric acid pinacol ester

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.

New synthesis method of N-substituted-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester

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.

Synthesis method of N-substituted-1,2,5,6-tetrahydropyridine-4-borate

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.

Synthesis method of N-substituted piperidine-4-borate

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.

Nitrogen aryl benzothiazole PARP inhibitors, preparation methods and uses thereof

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.

Ruthenium-catalyzed transformation of alkenyl triflates to alkenyl halides

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.