1H-Pyrrolo[2,3-b]pyridine, 1-[(4-methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

Base Information

• Chemical Name: 1H-Pyrrolo[2,3-b]pyridine, 1-[(4-methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
• CAS No.: 866545-91-7
• Molecular Formula: C20H23 B N2 O4 S
• Molecular Weight: 398.291
• Hs Code.: 2934999090
• Mol file: 866545-91-7.mol

Synonyms:1H-Pyrrolo[2,3-b]pyridine, 1-[(4-methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

Chemical Property of 1H-Pyrrolo[2,3-b]pyridine, 1-[(4-methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

Chemical Property:

• Vapor Pressure: 4.28E-13mmHg at 25°C
• Refractive Index: 1.595
• Boiling Point: 572°C at 760 mmHg
• PKA: 0.91±0.30(Predicted)
• Flash Point: 299.8°C
• PSA: 78.80000
• Density: 1.24
• LogP: 3.96170
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

97% ^*data from raw suppliers

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Pyrrolo[2,3-b]pyridine, 1-[(4-methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

There total 10 articles about 1H-Pyrrolo[2,3-b]pyridine, 1-[(4-methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 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%

bis(pinacol)diborane (73183-34-3) + 3-bromo-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine (226085-18-3) → 1-(4-methylbenzenesulfonyl)-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (866545-91-7)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; at 90 ℃; for 18h; Heating / reflux;

Reference yield: 81.5%

2,3-dimethyl-2,3-butane diol (76-09-5) + 1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-ylboronic acid (882562-39-2) → 1-(4-methylbenzenesulfonyl)-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (866545-91-7)

Guidance literature:

In dichloromethane; at 20 - 30 ℃; Large scale;

Reference yield:

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + 3-iodo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (664982-01-8) → 1-(4-methylbenzenesulfonyl)-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (866545-91-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In 1,4-dioxane; at 80 ℃; for 4h; Sealed tube;

DOI:10.1016/j.bmc.2019.06.029

upstream raw materials:

bis(pinacol)diborane

3-bromo-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine

2,3-dimethyl-2,3-butane diol

1-(4-methylbenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-ylboronic acid

Downstream raw materials:

3-(2-(methylthio)pyrimidin-4-yl)-1-(tolyl-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

3-(6-chloropyrimidin-4-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

C₂₅H₂₁N₅O₂S

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