4-(Morpholinosulfonyl)phenylboronic acid pinacol ester

Base Information

• Chemical Name: 4-(Morpholinosulfonyl)phenylboronic acid pinacol ester
• CAS No.: 1401222-64-7
• Molecular Formula: C₁₆H₂₄BNO₅S
• Molecular Weight: 353.247
• Mol file: 1401222-64-7.mol

Synonyms:4-(Morpholinosulfonyl)phenylboronic acid pinacol ester;4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylsulfonyl)morpholine

Chemical Property of 4-(Morpholinosulfonyl)phenylboronic acid pinacol ester

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

4-(Morpholinosulfonyl)phenylboronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 4-(Morpholinosulfonyl)phenylboronic Acid Pinacol Ester is an intermediate in the synthesis of pyridopyrazine derivatives for use in treatments of various proliferative cell diseases.

Technology Process of 4-(Morpholinosulfonyl)phenylboronic acid pinacol ester

There total 3 articles about 4-(Morpholinosulfonyl)phenylboronic acid pinacol ester 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: 89.0%

4-((4-bromophenyl)sulfonyl)morpholine (834-67-3) + bis(pinacol)diborane (73183-34-3) → 4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)sulfonyl)morpholine (1401222-64-7)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 80 ℃; for 3h;

DOI:10.1021/acs.jmedchem.5b00515

Reference yield:

4-bromobenzenesulfonyl chloride (98-58-8) → 4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)sulfonyl)morpholine (1401222-64-7)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 0.5 h / 20 °C

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / dimethyl sulfoxide / 4 h / 70 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; triethylamine; In dichloromethane; dimethyl sulfoxide;

Reference yield:

p-Iodobenzenesulfonyl chloride (98-61-3) → 4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)sulfonyl)morpholine (1401222-64-7)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 3 h / 20 °C

2: anhydrous potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 16 h / 90 °C / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous potassium acetate; triethylamine; In 1,4-dioxane; dichloromethane;

upstream raw materials:

4-((4-bromophenyl)sulfonyl)morpholine

bis(pinacol)diborane

4-bromobenzenesulfonyl chloride

p-Iodobenzenesulfonyl chloride

Downstream raw materials:

trans-4-(6-(butylamino)-3-(4-(morpholinosulfonyl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexanol

Refernces

• 1、 Devine, William,Woodring, Jennifer L.,Swaminathan, Uma,Amata, Emanuele,Patel, Gautam,Erath, Jessey,Roncal, Norma E.,Lee, Patricia J.,Leed, Susan E.,Rodriguez, Ana,Mensa-Wilmot, Kojo,Sciotti, Richard J.,Pollastri, Michael P.. "Protozoan Parasite Growth Inhibitors Discovered by Cross-Screening Yield Potent Scaffolds for Lead Discovery". supporting information. p. 5522 - 5537. Retrieved 2015/08/03.
• 2、 -. "SUBSTITUTED PYRIDOPYRAZINES AS NOVEL SYK INHIBITORS". Paragraph 0274; 0276. . Retrieved 2014/05/08.