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

Base Information

• Chemical Name: 1-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• CAS No.: 870717-93-4
• Molecular Formula: C20H22 B N O4 S
• Molecular Weight: 383.276
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60584674
• Wikidata: Q72498798
• Mol file: 870717-93-4.mol

Synonyms:870717-93-4;1-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;1-(Phenylsulfonyl)-3-indoleboronic acid pinacol ester;1-(Phenylsulfonyl)indole-3-boronic acid pinacol ester;1-(Benzenesulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole;1-(Phenylsulfonyl)-3-indolylboronic acid pinacol ester;MFCD08276778;(1-(PHENYLSULFONYL)-1H-INDOL-3-YL)BORONIC ACID PINACOL ESTER;1-(Phenylsulfonyl)-3-lndoleboronic acid pinacol ester;OMZLHWZHHPAZPW-UHFFFAOYSA-N;1-(benzenesulfonyl)-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;SCHEMBL3528138;DTXSID60584674;CS-B1224;VJB71793;AKOS016003614;PB29512;AM804446;AS-38211;SY096943;A849894;1-(Phenylsulfonyl)-3-indoleboronic acid, pinacol ester;1-(Phenylsulfonyl)-1H-indole-3-boronic Acid Pinacol Ester;1-(Phenylsulfonyl)-3-indolylboronic acid pinacol ester, 97%;1-(Benzenesulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Chemical Property of 1-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Chemical Property:

• Vapor Pressure: 2.03E-12mmHg at 25°C
• Melting Point: 120-125℃
• Refractive Index: 1.585
• Boiling Point: 556.4°C at 760 mmHg
• Flash Point: 290.3°C
• PSA: 65.91000
• Density: 1.21g/cm³
• LogP: 4.25830
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 383.1362595
• Heavy Atom Count: 27
• Complexity: 637

Purity/Quality:

97% ^*data from raw suppliers

1-(Phenylsulfonyl)-3-indolylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN(C3=CC=CC=C23)S(=O)(=O)C4=CC=CC=C4
• Uses: 1-(Phenylsulfonyl)-3-indolylboronic Acid Pinacol Ester is used as a reactant in the preparation of 3-(2-(pyridyl)ethenyl)indoles that are tryptophan dioxygenase (TDO) inhibitors and potential anticancer immunomodulators.

Technology Process of 1-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

There total 2 articles about 1-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 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: 67.0%

3-bromo-1-phenylsulfonyl indole (99655-68-2) + bis(pinacol)diborane (73183-34-3) → 1-(phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (870717-93-4)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 80 ℃;

DOI:10.1021/acs.jmedchem.1c00323

Reference yield:

indole (120-72-9) → 1-(phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (870717-93-4)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridinium perbromide hydrobromide / pyridine / 20 °C

2: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water; toluene / 0 - 20 °C

3: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; pyridinium perbromide hydrobromide; potassium acetate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In pyridine; water; N,N-dimethyl-formamide; toluene;

DOI:10.1039/c6md00675b

Reference yield: 90.0%

1-(phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (870717-93-4) + methyl 3-bromo-2-formylpyrrole-5-carboxylate → 4-(1-benzenesulfonyl-1H-indol-3-yl)-5-formyl-1H-pyrrole-2-carboxylic acid methyl ester

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In ethanol; water; toluene; at 110 ℃; for 2h; Microwave irradiation;

DOI:10.1016/j.tet.2014.11.035

upstream raw materials:

indole

3-bromo-1-phenylsulfonyl indole

bis(pinacol)diborane

Downstream raw materials:

ethyl N-({6-hydroxy-7-[1-(phenylsulfonyl)-1H-indol-3-yl]-5-quinoxalinyl}carbonyl)glycinate

(E)-1-(phenylsulfonyl)-3-(prop-1-enyl)-1H-indole

3-(1H-imidazol-2-yl)-1-(phenylsulfonyl)-1H-indole

tert-butyl 4-[2-[2-[1-(benzenesulfonyl)indol-3-yl]imidazol-1-yl]ethyl]piperidine-1-carboxylate

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