454482-11-2

Basic information

• Product Name: 1-METHYL-1,2,3,6-TETRAHYDROPYRIDINE-4-BORONIC ACID PINACOL ESTER
• Synonyms: 1-METHYL-1,2,3,6-TETRAHYDROPYRIDINE-4-BORONIC ACID PINACOL ESTER;4,4,5,5-tetramethyl-2-(1-methyl-3,5-dihydro-2H-pyrid-4-yl)-1,3,2-dioxaborolane;1-Methyl-1,2,3,6-tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;1-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine;1-Methyl-4-(tetraMethyl-1,3,2-dioxaborolan-2-yl)piperidine;Pyridine, 1,2,3,6-tetrahydro-1-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-;1-Methyl-1,2,3,6-tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, 2-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1-Methyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester 97%
• CAS NO: 454482-11-2
• Molecular Formula: C₁₂H₂₂BNO₂
• Molecular Weight: 223.12
• Mol File: 454482-11-2.mol

Chemical Properties

• Boiling Point: 252.5 °C at 760 mmHg
• Flash Point: 106.5 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 0.97g/cm³
• Vapor Pressure: 0.0151mmHg at 25°C
• Refractive Index: 1.467
• Storage Temp.: 2-8°C
• PKA: 9.25±0.40(Predicted)
• CAS DataBase Reference: 1-METHYL-1,2,3,6-TETRAHYDROPYRIDINE-4-BORONIC ACID PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-1,2,3,6-TETRAHYDROPYRIDINE-4-BORONIC ACID PINACOL ESTER(454482-11-2)
• EPA Substance Registry System: 1-METHYL-1,2,3,6-TETRAHYDROPYRIDINE-4-BORONIC ACID PINACOL ESTER(454482-11-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 454482-11-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-Methyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester is used as a substrate in the study of para-alkenylation reactions of toluene. This application is significant for advancing the understanding of palladium-catalyzed coupling reactions and the development of new synthetic methodologies.
Used in Chemical Research:
In the field of chemical research, 1-Methyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester serves as a valuable intermediate for the synthesis of complex organic molecules and pharmaceutical compounds. Its unique structure allows for the exploration of novel reaction pathways and the discovery of new chemical transformations.
Used in Pharmaceutical Industry:
1-Methyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester is used as a building block in the development of new drugs and pharmaceutical agents. Its ability to participate in various types of chemical reactions makes it a versatile component in the synthesis of bioactive molecules with potential therapeutic applications.

InChI:InChI=1/C12H24BNO2/c1-11(2)12(3,4)16-13(15-11)10-6-8-14(5)9-7-10/h10H,6-9H2,1-5H3

Upstream product

• 73183-34-3 bis(pinacol)diborane 
• 180692-27-7 1-methyl-4-[(trifluoromethanesulfonyl)oxy]-1,2,3,6-tetrahydropyridine 
• 1445-73-4 1-Methyl-4-piperidone 
• 1195-66-0 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 50-00-0 formaldehyd 
• 181219-01-2 4-pyridineboronic acid pinacol ester 
• 375853-82-0 tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate 
• 375853-82-0 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine 
• 74-88-4 methyl iodide 

Downstream Products

• 1383703-45-4 5-(1-methylpiperidin-4-yl)-3-{1-[4-(morpholin-4-ylcarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazole 
• 1421371-96-1 2-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitroaniline 
• 1421372-99-7 4-methoxy-6-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-N'-{4-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-yl}benzene-1,3-diamine 
• 1421373-06-9 4-methoxy-6-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-N'-{4-(1-methylindol-3-yl)pyrimidine-2-yl}benzene-1,3-diamine 
• 1421373-89-8 C₂₇H₂₇N₇O₂ 
• 1421371-94-9 6-methoxy-4-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-N'-{5-methyl-4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-yl}benzene-1,3-diamine 
• 1421371-95-0 N-[2-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitrophenyl]-5-methyl-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amine 
• 1421371-98-3 4-methoxy-6-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-N'-{5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl}benzene-1,3-diamine 
• 1421371-99-4 N'-{4-[1-(benzenesulfonyl)indol-3-yl]-5-chloropyrimidin-2-yl}-4-methoxy-6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)benzene-1,3-diamine 
• 1421372-00-0 4-[1-(benzenesulfonyl)indol-3-yl]-5-chloro-N-[2-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitrophenyl]pyrimidin-2-amine 
• 1421372-21-5 N-(5-chloro-4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-yl)-6-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)benzene-1,3-diamine 
• 1421372-22-6 5-chloro-N-[2-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitrophenyl]-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amine 
• 1421373-14-9 4-methoxy-6-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-N'-{4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-yl}benzene-1,3-diamine 
• 1421373-15-0 N-[2-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitrophenyl]-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amine 

Relevant articles and documents

Synthesis method of N-methyl-1, 2, 5, 6-tetrahydropyridine-4-boronic acid pinacol ester

The invention belongs to the field of synthesis of medical intermediates, and particularly relates to a synthesis method of N-methyl-1, 2, 5, 6-tetrahydropyridine-4-boronic acid pinacol ester. According to the method, N-Boc-1, 2, 5, 6-tetrahydropyridine-4-boronic acid pinacol ester is selected as a raw material, Boc protection is removed under an acidic condition, paraformaldehyde, a reducing reagent and HOBt are added for an N-methylation reaction, the method can effectively inhibit the occurrence of quaternary ammonium salt side reactions, the post-treatment is simple, and the method is suitable for industrial production. The crude product is recrystallized to obtain the N-methyl-1, 2, 5, 6-tetrahydropyridine-4-boronic acid pinacol ester product with the purity of more than 98.0%, and the two-step molar yield is more than 90%.

Preparation method of N-substituted-tetrahydropyridine-3/4-boric acid/ester

The invention discloses a preparation method of N-substituted tetrahydropyridine-3/4-boric acid/ester, and belongs to the technical field of organic boric acid chemistry. The method comprises the following steps: carrying out a reaction on pyridine-3/4-boric acid/ester and a halide to form a quaternary salt, and reducing the quaternary salt with sodium/potassium borohydride in an aprotic solvent to generate N-substituted-tetrahydropyridine-3/4-boric acid/ester. According to the method, easily-synthesized pyridine-3/4-boric acid/ester is used as a raw material, the product can be obtained through two continuous steps, and the reaction selectivity is high, so that the defect that palladium-catalyzed coupling or ultralow temperature is needed when substituted piperidone is adopted as a raw material is overcome, the method is verified on the hectogram scale, and a concise and efficient synthesis path is provided for preparation of the compound.

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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.

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