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

Base Information

• Chemical Name: 1H-Pyrrolo[2,3-b]pyridine, 1-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
• CAS No.: 942919-24-6
• Molecular Formula: C19H21BN2O4S
• Molecular Weight: 384.264
• Hs Code.: 2933990090
• Mol file: 942919-24-6.mol

Synonyms:1H-Pyrrolo[2,3-b]pyridine, 1-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;1-Phenylsulfonyl-7-azaind...;1-Phenylsulfonyl-7-azaindole-4-boronic acid pinacol ester;1-(benzenesulfonyl)-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine;1-(Benzenesulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine;1-(Phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pryrolo[2,3-b]pyridine

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

Chemical Property:

• Vapor Pressure: 8.58E-13mmHg at 25°C
• Boiling Point: 565.1°C at 760 mmHg
• Flash Point: 295.6°C
• PSA: 78.80000
• Density: 1.25g/cm³
• LogP: 3.65330

Purity/Quality:

97% ^*data from raw suppliers

1-Phenylsulfonyl-7-azaindole-4-boronicacidpinacolester 97.0% ^*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-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

There total 6 articles about 1H-Pyrrolo[2,3-b]pyridine, 1-(phenylsulfonyl)-4-(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: 92.0%

1-(benzenesulfonyl)-4-bromo-1H-pyrrolo[2,3-b]pyridine (889939-25-7) + bis(pinacol)diborane (73183-34-3) → 1-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo-[2,3-b]pyridine (942919-24-6)

Guidance literature:

With potassium acetate; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; at 100 ℃; for 0.75h;

Reference yield:

4-bromo-7-azaindole (348640-06-2) → 1-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo-[2,3-b]pyridine (942919-24-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: bis[1,2-bis(diphenylphosphino)ferrocene]-palladium⁽⁰⁾; potassium acetate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere

With bis[1,2-bis(diphenylphosphino)ferrocene]-palladium⁽⁰⁾; potassium acetate; sodium hydride; In N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.bmcl.2011.11.080

Reference yield:

1H-Pyrrolo[2,3-b]pyridine-7-oxide (55052-24-9) → 1-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo-[2,3-b]pyridine (942919-24-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetramethylammonium bromide; Methanesulfonic anhydride / N,N-dimethyl-formamide / 5 h / 0 - 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: bis[1,2-bis(diphenylphosphino)ferrocene]-palladium⁽⁰⁾; potassium acetate / N,N-dimethyl-formamide / 80 °C / Inert atmosphere

With bis[1,2-bis(diphenylphosphino)ferrocene]-palladium⁽⁰⁾; potassium acetate; tetramethylammonium bromide; sodium hydride; Methanesulfonic anhydride; In N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.bmcl.2011.11.080

upstream raw materials:

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

bis(pinacol)diborane

7-Azaindole

1H-Pyrrolo[2,3-b]pyridine-7-oxide

Downstream raw materials:

methyl 4-bromo-3-hydroxy-5-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-2-thiophenecarboxylate

methyl 4-bromo-3-fluoro-5-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-2-thiophenecarboxylate

4-(5-nitro-2-thienyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

3-(5-nitro-2-thienyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine