2-(1H-Pyrazol-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Base Information

• Chemical Name: 2-(1H-Pyrazol-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS No.: 1218791-02-6
• Molecular Formula: C₁₄H₁₈BN₃O₂
• Molecular Weight: 271.127
• Hs Code.: 2933399990
• DSSTox Substance ID: DTXSID30681942
• Wikidata: Q82606131
• Mol file: 1218791-02-6.mol

Synonyms:1218791-02-6;2-(1H-Pyrazol-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;2-(1H-PYRAZOL-1-YL)PYRIDINE-5-BORONIC ACID, PINACOL ESTER;2-pyrazol-1-yl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;2-(1H-Pyrazol-1-yl)pyridine-5-boronic acid pinacol ester;SCHEMBL860013;2-(1H-Pyrazol-1-yl)pyridine-5-boronic acid,pinacol ester;DTXSID30681942;MFCD11878223;AKOS016001224;AT14246;FS-6011;MB10902;CS-0175707;FT-0707543;2-PYRAZOL-1-YL-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(1h-pyrazol-1-yl)pyridine

Chemical Property of 2-(1H-Pyrazol-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Chemical Property:

• Boiling Point: 395.9±27.0 °C(Predicted)
• PKA: 1.56±0.31(Predicted)
• Density: 1.13±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 271.1492070
• Heavy Atom Count: 20
• Complexity: 348

Purity/Quality:

97% ^*data from raw suppliers

2-(1H-pyrazol-1-yl)pyridine-5-boronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN=C(C=C2)N3C=CC=N3

Technology Process of 2-(1H-Pyrazol-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

There total 4 articles about 2-(1H-Pyrazol-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 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: 73.0%

bis(pinacol)diborane (73183-34-3) + 5-bromo-2-(1H-pyrazol-1-yl)pyridine (433922-57-7) → 2-(1H-pyrazol-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1218791-02-6)

Guidance literature:

bis(pinacol)diborane; 5-bromo-2-(1H-pyrazol-1-yl)pyridine; With potassium acetate; In 1,4-dioxane; for 0.5h; Inert atmosphere;

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80 ℃; for 3h;

DOI:10.1007/s00044-020-02638-w

Reference yield:

1,4-dioxane (123-91-1,28347-88-8,28347-91-3,39449-24-6,54841-74-6) + 5-bromo-2-(1H-pyrazol-1-yl)pyridine (433922-57-7) → 2-(1H-pyrazol-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1218791-02-6)

Guidance literature:

With potassium acetate;

Reference yield:

2,5-dibromopyridine (624-28-2) → 2-(1H-pyrazol-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1218791-02-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NH-pyrazole / N,N-dimethyl-formamide

2: potassium acetate

With NH-pyrazole; potassium acetate; In N,N-dimethyl-formamide;

upstream raw materials:

1,4-dioxane

5-bromo-2-(1H-pyrazol-1-yl)pyridine

2,5-dibromopyridine

bis(pinacol)diborane

Downstream raw materials:

2-(6-(1H-pyrazol-1-yl)pyridin-3-yl)-10-(3-(trifluoromethyl)phenyl)pyrido[3,2-c][1,5] naphthyridin-9(10H)-one