2-Ethoxycarbonylindole-5-boronic acid pinacol ester

Base Information

• Chemical Name: 2-Ethoxycarbonylindole-5-boronic acid pinacol ester
• CAS No.: 736990-02-6
• Molecular Formula: C17H22BNO4
• Molecular Weight: 315.17200
• Hs Code.: 2934999090
• Mol file: 736990-02-6.mol

Synonyms:5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole-2-carboxylic acid ethyl ester;HIN1677;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole-2-carboxylic acid ethyl ester;

Chemical Property of 2-Ethoxycarbonylindole-5-boronic acid pinacol ester

Chemical Property:

• Vapor Pressure: 5.83E-09mmHg at 25°C
• Boiling Point: 468.8oC at 760 mmHg
• PKA: 15.02±0.30(Predicted)
• Flash Point: 237.3oC
• PSA: 60.55000
• Density: 1.16g/cm3
• LogP: 2.64380
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

ethyl5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Ethoxycarbonylindole-5-boronic acid pinacol ester

There total 4 articles about 2-Ethoxycarbonylindole-5-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: 97.0%

ethyl 5-bromoindolecarboxylate (16732-70-0) + bis(pinacol)diborane (73183-34-3) → 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole-2-carboxylic acid ethyl ester (736990-02-6)

Guidance literature:

With potassium acetate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tricyclohexylphosphine; In 1,4-dioxane; at 80 ℃; for 3h;

Reference yield:

5-bromo-2-indolecarboxylic acid (7254-19-5) + bis(pinacol)diborane (73183-34-3) → 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole-2-carboxylic acid ethyl ester (736990-02-6)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In 1,4-dioxane; for 17h; Inert atmosphere; Reflux;

Reference yield:

5-bromo-2-indolecarboxylic acid (7254-19-5) → 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole-2-carboxylic acid ethyl ester (736990-02-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 12 h / 80 °C

2: potassium acetate; bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane; ethyl acetate / 17 h / Reflux; Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; sulfuric acid; potassium acetate; In 1,4-dioxane; ethyl acetate;

upstream raw materials:

ethyl 5-bromoindolecarboxylate

bis(pinacol)diborane

5-bromo-2-indolecarboxylic acid

Downstream raw materials:

1-benzyl-4-(2-ethoxycarbonyl-1H-indol-5-yl)-pyridinium bromide

4-[2-(4-fluoro-phenylcarbamoyl)-1H-indol-5-yl]-piperidine-1-carboxylic acid tert-butyl ester

5-piperidin-4-yl-1H-indole-2-carboxylic acid (4-fluoro-phenyl)-amide

5-(1-isopropyl-piperidin-4-yl)-1H-indole-2-carboxylic acid (3-fluoro-phenyl)-amide

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