N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester

Base Information

• Chemical Name: N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester
• CAS No.: 1073354-51-4
• Molecular Formula: C21H24BNO4S
• Molecular Weight: 397.303
• Hs Code.: 2934999090
• Mol file: 1073354-51-4.mol

Synonyms:1-(TOLUENE-4-SULFONYL)-1H-INDOLE-3-BORONIC ACID PINACOL ESTER;N-(TOLUENESULFONYL)INDOLE-3-BORONIC ACID PINACOL ESTER;N-(P-TOLUENESULFONYL)INDOLE-3-BORONIC ACIS PINACOL ESTER

Chemical Property of N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester

Chemical Property:

• PSA: 65.91000
• LogP: 4.56670

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-(p-Toluenesulfonyl)indole-3-boronic acid pinacol ester

There total 6 articles about N-(p-Toluenesulfonyl)indole-3-boronic 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: 30.0%

1-(p-toluenesulfonyl)-1H-indole (31271-90-6) + bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-p-toluenesulfonyl-1H-indole (1073354-51-4)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; for 1.65h; Milling;

DOI:10.1002/chem.201900685

Reference yield:

3-iodo-1-tosyl-1-indole (170456-80-1) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-p-toluenesulfonyl-1H-indole (1073354-51-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In 1,4-dioxane; at 80 ℃; for 4h; Inert atmosphere; Schlenk technique;

DOI:10.1002/ejoc.201300133

Reference yield:

indole (120-72-9) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-p-toluenesulfonyl-1H-indole (1073354-51-4)

Guidance literature:

Multi-step reaction with 3 steps

1: iodine; potassium hydroxide / N,N-dimethyl-formamide / 0.75 h / 20 °C

2: potassium hydroxide / N,N-dimethyl-formamide / 3 h / 20 °C

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / 1,4-dioxane / 4 h / 80 °C / Inert atmosphere; Schlenk technique

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; iodine; triethylamine; potassium hydroxide; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201300133

upstream raw materials:

3-Iodo-1H-indole

indole

3-iodo-1-tosyl-1-indole

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

Downstream raw materials:

1H,1'H-[3,3']biindolyl

1,1'-bis-(toluene-4-sulfonyl)-1H,1'H-[3,3']biindolyl

3-methyl-N-(p-toluenesulfonyl)indole

tert-butyl 4-(1-tosyl-1H-indol-3-yl)pent-4-enoate