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

Base Information

• Chemical Name: 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine
• CAS No.: 1644629-23-1
• Molecular Formula: C₁₄H₁₉BN₂O₂
• Molecular Weight: 258.128
• Mol file: 1644629-23-1.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

95% purity ^*data from raw suppliers

1-Methyl-7-azaindole-4-boronicacidpinacolester 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine 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%

1-Methyl-4-chloro-1H-pyrrolo<2,3-b>pyridine (74420-05-6) + bis(pinacol)diborane (73183-34-3) → 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (1644629-23-1)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 100 ℃; for 14h;

DOI:10.1021/ja512306a

Reference yield: 82.0%

4-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine (1234616-25-1) + bis(pinacol)diborane (73183-34-3) → 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (1644629-23-1)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 20 - 90 ℃; for 2.5h; Inert atmosphere;

Reference yield:

4-bromo-7-azaindole (348640-06-2) → 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (1644629-23-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

1.2: 0.5 h / 20 °C

2.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 2.5 h / 20 - 90 °C / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; sodium hydride; In 1,4-dioxane; N,N-dimethyl-formamide;

upstream raw materials:

1-Methyl-4-chloro-1H-pyrrolo<2,3-b>pyridine

bis(pinacol)diborane

4-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine

4-bromo-7-azaindole

Refernces

• 1、 Zeng, Rong,Dong, Guangbin. "Rh-catalyzed decarbonylative coupling with alkynes via C-C activation of isatins". supporting information. p. 1408 - 1411. Retrieved 2015/02/19.