1H-Pyrrolo[2,3-b]pyridine, 5-chloro-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, 5-chloro-1-[(4-Methylphenyl)sulfonyl]-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)
• CAS No.: 866546-11-4
• Molecular Formula: C20H22BClN2O4S
• Molecular Weight: 432.736
• Hs Code.: 2933998090
• Mol file: 866546-11-4.mol

Synonyms:5-chloro-1-[(4-methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3.2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]-pyridine;5-chloro-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1-(toluene-4-sulfonyl)-1H-[2,3-b]pyridine;1H-Pyrrolo[2,3-b]pyridine,5-chloro-1-[(4-methylphenyl)sulfonyl]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl);5-chloro-3-(4,4,5,5-tetramethyl-1,3.2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]-pyridine;5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine;5-Chloro-1-tosyl-7-azaindole-3-boronic acid pinacol ester;

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

Chemical Property:

• Boiling Point: 584.5±60.0 °C(Predicted)
• PKA: -1.22±0.30(Predicted)
• PSA: 78.80000
• Density: 1.31±0.1 g/cm3(Predicted)
• LogP: 4.61510
• Storage Temp.: 2-8°C

Purity/Quality:

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

5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1h-pyrrolo[2,3-b]pyridine 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
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MSDS Files:

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

There total 8 articles about 1H-Pyrrolo[2,3-b]pyridine, 5-chloro-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: 82.0%

3-bromo-5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine (866546-10-3) + bis(pinacol)diborane (73183-34-3) → 5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine (866546-11-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; In 1,4-dioxane; water; at 95 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b00301

Reference yield:

3-bromo-5-chloro-1 H-pyrrolo[2,3-b]pyridine (866546-09-0) → 5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine (866546-11-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.83 h / 0 °C / Inert atmosphere

1.2: 1.5 h / 0 - 25 °C

2.1: potassium acetate / palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,2-dimethoxyethane / 6 h / 86 °C / Inert atmosphere

With potassium acetate; sodium hydride; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; In 1,2-dimethoxyethane; N,N-dimethyl-formamide; mineral oil;

Reference yield:

5-chloro-1H-pyrrolo[2,3-b]pyridine (866546-07-8) → 5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine (866546-11-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: bromine; acetic acid / 3 h / 90 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.83 h / 0 °C / Inert atmosphere

2.2: 1.5 h / 0 - 25 °C

3.1: potassium acetate / palladium bis[bis(diphenylphosphino)ferrocene] dichloride / 1,2-dimethoxyethane / 6 h / 86 °C / Inert atmosphere

With bromine; potassium acetate; sodium hydride; acetic acid; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; In 1,2-dimethoxyethane; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

3-bromo-5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine

bis(pinacol)diborane

5-chloro-2-pyridylamine

5-chloro-3-iodo-2-aminopyridine

Downstream raw materials:

methyl 6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-pyrazine-2-carboxylate

potassium (5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)trifluoroborate

(2R)-1-(6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrazin-2-yl)-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide hydrochloride

diethyl (6-{5-chloro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-pyrazin-2-yl)propanedioate

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