1-BOC-indole-3-boronic acid, pinacol ester

Base Information

• Chemical Name: 1-BOC-indole-3-boronic acid, pinacol ester
• CAS No.: 942070-45-3
• Molecular Formula: C19H26BNO4
• Molecular Weight: 343.231
• Hs Code.: 2934999090
• Mol file: 942070-45-3.mol

Synonyms:N-boc-Indole-3-toronicacidpinacolester;

Chemical Property of 1-BOC-indole-3-boronic acid, pinacol ester

Chemical Property:

• Vapor Pressure: 0.00934mmHg at 25°C
• Melting Point: 163-165 °C
• Boiling Point: 265.1°C at 760 mmHg
• Flash Point: 115.8°C
• PSA: 49.69000
• Density: 0.938g/cm³
• LogP: 3.72370
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-BOC-indole-3-boronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-BOC-indole-3-boronic acid, pinacol ester

There total 8 articles about 1-BOC-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: 99.0%

indole-1-carboxylic acid tert-butyl ester (75400-67-8) + bis(pinacol)diborane (73183-34-3) → tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (942070-45-3)

Guidance literature:

With [iridium(I)(1,5-cyclooctadiene)(1,10-phenantroline)chloride]; In octane; at 80 ℃; for 16h; Reagent/catalyst; Solvent; Catalytic behavior; Inert atmosphere; Schlenk technique;

DOI:10.1021/om500420d

Reference yield: 93.0%

indole-1-carboxylic acid tert-butyl ester (75400-67-8) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (942070-45-3)

Guidance literature:

With [iridium(I)(1,5-cyclooctadiene)(1,10-phenantroline)chloride]; In octane; at 80 ℃; for 16h; Concentration; Inert atmosphere; Schlenk technique;

DOI:10.1021/om500420d

Reference yield: 67.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + tert-butyl 3-iodo-1H-indol-1-carboxylate (192189-07-4) → tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (942070-45-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1002/cmdc.202000604

upstream raw materials:

indole-1-carboxylic acid tert-butyl ester

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

3-bromoindole-1-carboxylic acid tert-butyl ester

bis(pinacol)diborane

Downstream raw materials:

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

3-(4-{(S)-1-[(R)-1-(4-Methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-2-yl)-indole-1-carboxylic acid tert-butyl ester

4-(1H-indol-3-yl)pyrimidin-2-amine

3-(pyrimidin-2-yl)-1H-indole

Refernces

• 1、 Garrison, Michelle A.,Mahoney, Andrew R.,Wuest, William M.. "Tricepyridinium-inspired QACs yield potent antimicrobials and provide insight into QAC resistance". . p. 463 - 466. Retrieved 2020/10/19.
• 2、 Slack, Eric D.,Colacot, Thomas J.. "Understanding the Activation of Air-Stable Ir(COD)(Phen)Cl Precatalyst for C-H Borylation of Aromatics and Heteroaromatics". . p. 1561 - 1565. Retrieved 2021/02/20.