1-(Benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-boronic acid pinacol ester

Base Information

• Chemical Name: 1-(Benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-boronic acid pinacol ester
• CAS No.: 886547-94-0
• Molecular Formula: C19H21BN2O4S
• Molecular Weight: 384.264
• Hs Code.: 2934999090
• Mol file: 886547-94-0.mol

Synonyms:1-(benzenesulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine

Chemical Property of 1-(Benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-boronic acid pinacol ester

Chemical Property:

• Melting Point: 355-360°C
• Boiling Point: 565.1 °C at 760 mmHg
• Flash Point: 295.6 °C
• PSA: 78.80000
• Density: 1.25 g/cm³
• LogP: 3.65330

Purity/Quality:

97% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-(Benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-boronic acid pinacol ester

There total 8 articles about 1-(Benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-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: 100.0%

3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (887115-53-9) + bis(pinacol)diborane (73183-34-3) → 1-(phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (886547-94-0)

Guidance literature:

With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In N,N-dimethyl-formamide; at 90 ℃; for 2h;

Reference yield: 92.0%

3-bromo-1-(benzenesulfonyl)-1H-pyrrolo [2,3-b]pyridine (880769-95-9) + bis(pinacol)diborane (73183-34-3) → 1-(phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (886547-94-0)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2006.06.073

Reference yield:

7-Azaindole (271-63-6) → 1-(phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (886547-94-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-Bromosuccinimide / tetrahydrofuran / 4 h / -40 - 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C

2.2: 0 - 20 °C

3.1: potassium acetate / bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 0.33 h / 140 °C / Inert atmosphere; Microwave irradiation

With N-Bromosuccinimide; potassium acetate; sodium hydride; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; N,N-dimethyl-formamide;

upstream raw materials:

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

bis(pinacol)diborane

7-Azaindole

1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine

Downstream raw materials:

4-[7-(1-Benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-4-oxo-3,4-dihydro-phthalazin-1-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester

6-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-(piperidin-4-ylmethyl)phthalazin-1(2H)-one

C₁₈H₁₁N₅O₂S

N-cyclohexyl-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-amine