1-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)ethanone

Base Information

• Chemical Name: 1-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)ethanone
• CAS No.: 741709-59-1
• Molecular Formula: C13H18BNO3
• Molecular Weight: 247.102
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID70694490
• Wikidata: Q82623600
• Mol file: 741709-59-1.mol

Synonyms:741709-59-1;1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)ethanone;6-Acetylpyridine-3-boronic acid pinacol ester;1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]ethanone;1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)ethan-1-one;1-[5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]ethan-1-one;SCHEMBL2640279;(6-ACETYLPYRIDIN-3-YL)BORONIC ACID PINACOL ESTER;DTXSID70694490;ISRQZHALMLGEGD-UHFFFAOYSA-N;MFCD12923434;1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]ethanone;AKOS015949997;MB12193;AC-30414;PS-12949;CS-0139904;FT-0708795;F50469;A850802;J-503386;2-ACETYLPYRIDINE-5-BORONIC ACID PINACOL ESTER;1-(5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridin-2-yl)ethanone

Chemical Property of 1-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)ethanone

Chemical Property:

• Boiling Point: 363.7±27.0 °C(Predicted)
• PKA: 2.99±0.12(Predicted)
• PSA: 48.42000
• Density: 1.08±0.1 g/cm3(Predicted)
• LogP: 1.58340
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 247.1379736
• Heavy Atom Count: 18
• Complexity: 327

Purity/Quality:

99.3% ^*data from raw suppliers

1-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)ethanone 95+% ^*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)C(=O)C

Technology Process of 1-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)ethanone

There total 1 articles about 1-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)ethanone 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: 90.0%

bis(pinacol)diborane (73183-34-3) + 1-(5-bromopyridin-2-yl)ethanone (214701-49-2) → 1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaboralan-2-yl)pyridin-2-yl)ethan-1-one (741709-59-1)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; for 4h; Inert atmosphere; Reflux;

Reference yield: 55.0%

1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaboralan-2-yl)pyridin-2-yl)ethan-1-one (741709-59-1) + tert-butyl 2-(8-bromo-6-cyano-3-(3-fluoro-4-methoxyphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)pyrrolidine-1-carboxylate → 8-(6-acetylpyridin-3-yl)-3-(3-fluoro-4-methoxyphenyl)-4-oxo-2-(pyrrolidin-2-yl)-3,4-dihydroquinazoline-6-carbonitrile

Guidance literature:

1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaboralan-2-yl)pyridin-2-yl)ethan-1-one; tert-butyl 2-(8-bromo-6-cyano-3-(3-fluoro-4-methoxyphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)pyrrolidine-1-carboxylate; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In 1,4-dioxane; water; at 85 ℃; for 16h; Inert atmosphere;

at 20 - 40 ℃; for 24h;

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃;

Reference yield:

1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaboralan-2-yl)pyridin-2-yl)ethan-1-one (741709-59-1) + 2-(4-(benzyloxy)phenyl)-8-iodo-5,7-dimethoxy-4H-chromen-4-one → C23H17NO6

Guidance literature:

1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaboralan-2-yl)pyridin-2-yl)ethan-1-one; 2-(4-(benzyloxy)phenyl)-8-iodo-5,7-dimethoxy-4H-chromen-4-one; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In water; N,N-dimethyl-formamide; at 110 ℃;

With aluminum (III) chloride; at 85 ℃;

With boron tribromide; at 20 ℃;

DOI:10.1016/j.bcp.2021.114620

upstream raw materials:

bis(pinacol)diborane

1-(5-bromopyridin-2-yl)ethanone

Refernces

• 1、 -. "FUSED TRICYCLIC COMPOUNDS AS mTOR INHIBITORS". Page/Page column 64. . Retrieved 2013/03/26.
• 2、 -. "HETEROARYLOXYCARBOCYCLYL COMPOUNDS AS PDE10 INHIBITORS". Page/Page column 68. . Retrieved 2011/12/02.