286961-14-6

Basic information

• Product Name: N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester
• Synonyms: N-BOC-1,2,5,6-TETRAHYDROPYRIDINE-4-(PINACOLATO)BORONATE;(N-TERT-BUTOXYCARBONYL)-1,2,3,6-TETRAHYDROPYRIDINE-4-BORONIC ACID PINACOL ESTER;4-(4,4,5,5-TETRAMETHYL-[1,3,2]-DIOXABOROLAN-2-YL)-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;3,6-DIHYDRO-2H-PYRIDINE-1-TERT-BUTOXYCARBONYL-4-BORONIC ACID, PINACOL ESTER;1-N-BOC-4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-3,6-DIHYDRO-2H-PYRIDINE;PyridineC5H5N;3,6-Dihydro-2H-pyridine-1-N-Boc-4-boronic acid pinacol ester;1-N-BOC-4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-3,6-DIHYDRO-2H-PYRIDINE 98+%
• CAS NO: 286961-14-6
• Molecular Formula: C₁₆H₂₈BNO₄
• Molecular Weight: 309.21
• EINECS: 1312995-182-4
• Product Categories: API intermediates;Organoborons;Pyridine
• Mol File: 286961-14-6.mol
• Article Data: 67

Chemical Properties

• Melting Point: 114.0 to 118.0 °C
• Boiling Point: 348.007 °C at 760 mmHg
• Flash Point: 164.269 °C
• Appearance: /Solid
• Density: 1.055 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.488
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -1.21±0.40(Predicted)
• Water Solubility: Soluble in most organic solvents. Insoluble in water.
• CAS DataBase Reference: N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester(286961-14-6)
• EPA Substance Registry System: N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester(286961-14-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37-60
• WGK Germany: 3
• TSCA: No
• HazardClass: IRRITANT
• Hazardous Substances Data: 286961-14-6(Hazardous Substances Data)

Usage

Chemical Properties

off-white powder

Uses

Different sources of media describe the Uses of 286961-14-6 differently. You can refer to the following data:
1. Reagent used for suzuki-Miyaura cross-coupling using palladium phosphine catalyst, palladium-catalyzed ligand-controlled regioselective Suzuki coupling, wrenchnolol derivative optimized for gene activation in cells. Also used in Preparation of several enzymatic inhibitors and receptor ligands, orally active anaplastic lymphoma kinase inhibitors and oxazolecarboxamides as diacylglycerol acyltransferase-1 inhibitors for treatment of obesity and diabetes.
2. N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester is an intermediate for organic synthesis and pharmaceutical research and development, and can be used for suzuki reaction.

InChI:InChI=1/C16H28BNO4/c1-14(2,3)20-13(19)18-10-8-12(9-11-18)17-21-15(4,5)16(6,7)22-17/h8H,9-11H2,1-7H3

Upstream product

• 138647-49-1 4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 10221-56-4 bis(pinacolato)diborane 
• 24608-52-4 tert-butyl chloroformate 
• 181219-01-2 4-pyridineboronic acid pinacol ester 
• 159503-91-0 tert-butyl 4-bromo-5,6-dihydropyridine-1(2H)-carboxylate 
• 1195-66-0 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 73183-34-3 bis(pinacol)diborane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1386393-97-0 tert-butyl 4-[(1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl)oxy]-3,6-dihydropyridine-1(2H)-carboxylate 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 41979-39-9 4-piperidone hydrochloride 
• 76-09-5 2,3-dimethyl-2,3-butane diol 

Downstream Products

• 138647-51-5 4-(4-methoxyphenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 949096-71-3 4-(2,4,6-trifluoro-3-isobutyrylaminophenyl)piperidine-1-carboxylic acid tert-butyl ester 
• 487057-87-4 4-(5-isobutyrylamino-2-methylphenyl)piperidine-1-carboxylic acid tert-butyl ester 
• 387827-31-8 4-(3-isobutyrylaminophenyl)piperidine-1-carboxylic acid tert-butyl ester 
• 949096-72-4 4-(3-isobutyrylamino-2-methylphenyl)piperidine-1-carboxylic acid tert-butyl ester 
• 762298-09-9 2-methyl-N-[2,4,6-trifluoro-3-(4-piperidinyl)phenyl]propanamide 
• 486451-46-1 2-methyl-N-[4-methyl-3-(4-piperidinyl)phenyl]propanamide 
• 387827-32-9 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide 
• 762297-43-8 N-(2-methyl-3-piperidin-4-ylphenyl)isobutyramide 
• 949096-75-7 N-(3-{1-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)propyl]piperidin-4-yl}-2,4,6-trifluorophenyl)isobutyramide 
• 949096-76-8 N-(3-{1-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)propyl]piperidin-4-yl}-4-methylphenyl)isobutyramide 
• 487057-88-5 N-(3-{1-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)ethyl]piperidin-4-yl}-phenyl)isobutyramide 
• 387826-55-3 N-(3-{1-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)propyl]piperidin-4-yl}-phenyl)isobutyramide 
• 387826-52-0 N-(3-{1-[4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butyl]-4-piperidinyl}phenyl)-2-methylpropanamide 

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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.

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.