tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Base Information

• Chemical Name: tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate
• CAS No.: 286961-14-6
• Molecular Formula: C₁₆H₂₈BNO₄
• Molecular Weight: 309.214
• Hs Code.: 29349990
• European Community (EC) Number: 689-148-0
• DSSTox Substance ID: DTXSID60405158
• Nikkaji Number: J1.315.440F
• Wikidata: Q72450830
• Mol file: 286961-14-6.mol

Synonyms:286961-14-6;N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate;Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate;N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester;3,6-DIHYDRO-2H-PYRIDINE-1-N-BOC-4-BORONIC ACID PINACOL ESTER;tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate;TERT-BUTYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDROPYRIDINE-1(2H)-CARBOXYLATE;3,6-DIHYDRO-2H-PYRIDINE-1-N-BOC-4-BORONIC ACID, PINACOL ESTER;MFCD03840345;tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate;TERT-BUTYL 5,6-DIHYDRO-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PYRIDINE-1(2H)-CARBOXYLATE;1-Boc-1,2,3,6-tetrahydropyridine-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;1-N-Boc-4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine;4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester;4-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester;tert-butyl 4-[4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate;(N-tert-Butoxycarbonyl)-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester;SCHEMBL39349;DTXSID60405158;VVDCRJGWILREQH-UHFFFAOYSA-N;3,6-Dihydro-2H-pyridine-1-tert-butoxycarbonyl-4-boronic acid;BCP05435;CS-B0439;N-BOC-1,2,5,6-TETRAHYDROPYRIDINE-4-(PINACOLATO)BORONATE;[1-Boc-1,2,5,6-tetrahydropyridine-4-yl]boronic acid pinacol ester;AKOS005258661;PB29279;PB45555;(1-(TERT-BUTOXYCARBONYL)-1,2,3,6-TETRAHYDROPYRIDIN-4-YL)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;4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester;AC-24255;HY-40249;SY009245;tert-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate;TERT-BUTYL4-(4,4,5,5-TETRAMET;AM20090370;B4051;FT-0649004;A15453;EN300-122712;4X-9028;J-511403;F1905-7232;Z1508685432;1-boc-3,6-dihydro-2h-pyridine-4-boronic acid pinacol ester;1-N-Boc-3,6-Dihydro-2H-pyridine-4-boronic acid pinacol ester;1,2,3,6-Tetrahydropyridine-4-boronic acid, pinacol ester, N-BOC protected;N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester, 95%;(1-TERT-BUTOXYCARBONYL-1,2,3,6-TETRAHYDROPYRIDIN-4-YL)BORONIC ACID PINACOL ESTER;(N-TERT-BUTOXYCARBONYL-1,2,3,6-TETRAHYDROPYRIDIN-4-YL)BORONIC ACID PINACOL ESTER;1-(tert-Butoxycarbonyl)-1,2,3,6-tetrahydro-4-pyridylboronic Acid Pinacol Ester;1-BOC-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine;1-N-Boc-4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine;3,6-DIHYDRO-2H-PYRIDINE-1-TERT-BUTOXYCARBONYL-4-BORONIC ACIDPINACOL ESTER;N-(TERT-BUTOXYCARBONYL)-3,6-DIHYDRO-2H-PYRIDINE-4-BORONIC ACID PINACOL ESTER;n-tert-butoxycarbonyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester;N-tert-butyloxycarbonyl-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester;1,1-dimethylethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate;1,2,3,6-tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine-1-carboxylic acid ter-butylester;1-(tert-Butoxycarbonyl)-1,2,3,6-tetrahydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;1-tert-butoxycarbonyl-4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl)-1,2,3,6-tetrahydropyridine;2-[1-(tert-Butoxycarbonyl)-1,2,3,6-tetrahydro-4-pyridyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-methylpropan-2-yl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate;3,6-DIHYDRO-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1(2H)-PYRIDINECARBOXYLIC ACID, 1,1-DIMETHYLETHYL ESTER;3,6-dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1(2H)-pyridinecarboxylicacid 1,1-dimethylethyl ester;4-(4 pound not4 pound not5 pound not5-tetramethyl-1 pound not3 pound not2-dioxaborolan-2-yl)-3 pound not6-dihydro-2H-pyridine-1-carboxylic acid tertbutyl ester;4-(4,4,5,5-tetra-methyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester;4-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester;4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-3,6-dihydro-2 h-pyridine-1-carboxylic acid tert-butyl ester;4-(4,4,5,5-Tetramethyl-[1,3,2]-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert butyl ester;4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2h-pyridin-1-carboxylic acid tert-butyl ester;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2h-pyridine-1-carboxylic acid tert butyl ester;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylic acid tert-butyl ester;4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester;t-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2h)-carboxylate;tert-butyl 4(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)carboxylate;tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborol-an-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -5,6-dihydropyridine-1(2H)-carboxylate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydro-1-pyridinecarboxylate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydro-pyridine-1-carboxylate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1 (2H)-pyridinecarboxylate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridin-1-carboxylate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1 (2H)-carboxylate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2 H)-carboxylate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5, 6-dihydropyridine-1(2H)-carboxylate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydro-2H-pyridine-1-carboxylate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1(2H)-carboxylate;Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1-(2H)-carboxylate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2 H)-carboxylate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1-(2H)-carboxylate;tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-6-dihydropyridine-1(2H)-carboxylate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate;tert-butyl 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate;tert-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate;tert-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate;tert-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate;tert-Butyl4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydro-1-pyridinecarboxylate;TERT-BUTYL4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-3,6-DIHYDRO-2H-PYRIDINE-1-CARBOXYLATE;tert-butyl4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Chemical Property of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 100-102 °C
• Refractive Index: 1.488
• Boiling Point: 348.007 °C at 760 mmHg
• PKA: -1.21±0.40(Predicted)
• Flash Point: 164.269 °C
• PSA: 48.00000
• Density: 1.055 g/cm³
• LogP: 3.12290
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility.: Soluble in most organic solvents. Insoluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 309.2111385
• Heavy Atom Count: 22
• Complexity: 463

Purity/Quality:

99% ^*data from raw suppliers

N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37-60

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CCN(CC2)C(=O)OC(C)(C)C
• Uses: 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. 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.

Technology Process of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

There total 23 articles about tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (138647-49-1) + bis(pinacol)diborane (73183-34-3) → tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate (375853-82-0,286961-14-6)

Guidance literature:

With 1,1'-bis(diphenylphosphino)ferrocene; potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; at 80 ℃;

Reference yield: 98.0%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + bis(pinacol)diborane (73183-34-3) → tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate (375853-82-0,286961-14-6)

Guidance literature:

N-tert-butyloxycarbonylpiperidin-4-one; With N,N-phenylbistrifluoromethane-sulfonimide; lithium diisopropyl amide; In tetrahydrofuran; at -78 - 0 ℃;

bis(pinacol)diborane; With 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃;

DOI:10.1021/jm701590h

Reference yield: 80.0%

bis(pinacolato)diborane (10221-56-4) + 4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (138647-49-1) → tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate (375853-82-0,286961-14-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃;

DOI:10.1016/j.bmcl.2008.08.020

upstream raw materials:

4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

bis(pinacol)diborane

N-tert-butyloxycarbonylpiperidin-4-one

bis(pinacolato)diborane

Downstream raw materials:

tert-butyl 4-(4-cyano-3-methylphenyl)-3,6-dihydropyridine-1(2H)-carboxylate

tert-butyl 4-(5-{[(benzyloxy)carbonyl]amino}-2,4-difluorophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate

tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate

tert-butyl 4-(4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Refernces

• 1、 -. "AZAINDOLE DERIVATIVE AND USE THEREOF AS FGFR AND C-MET INHIBITOR". Paragraph 0204-0205. . Retrieved 2021/05/29.
• 2、 -. "Tetrahydroisoquinoline amide compounds containing quaternary ammonium ion and pharmaceutical use thereof". Paragraph 0333-0336. . Retrieved 2019/07/11.