2-Methylindazole-5-boronic acid pinacol ester

Base Information

• Chemical Name: 2-Methylindazole-5-boronic acid pinacol ester
• CAS No.: 1189746-27-7
• Molecular Formula: C14H21BN2O3
• Molecular Weight: 258.128
• Hs Code.: 2933990090
• Mol file: 1189746-27-7.mol

Synonyms:2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole;

Chemical Property of 2-Methylindazole-5-boronic acid pinacol ester

Chemical Property:

• Boiling Point: 404.4±18.0 °C(Predicted)
• PKA: 1.27±0.30(Predicted)
• PSA: 36.28000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 1.87250
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

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

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Methylindazole-5-boronic acid pinacol ester

There total 3 articles about 2-Methylindazole-5-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: 76.0%

2-Methyl-5-bromo-2H-indazole (465529-56-0) + bis(pinacol)diborane (73183-34-3) → 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole (1189746-27-7)

Guidance literature:

With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; at 100 ℃; for 1.5h; Inert atmosphere;

Reference yield: 72.7%

→ 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole (1189746-27-7)

Guidance literature:

With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium acetate; In 1,4-dioxane; at 100 ℃; for 18h; Inert atmosphere;

Reference yield:

5-bromo-1H-indazole (53857-57-1) → 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole (1189746-27-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 3 h / 20 °C

2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 90 °C / Inert atmosphere

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

upstream raw materials:

2-Methyl-5-bromo-2H-indazole

bis(pinacol)diborane

5-bromo-1H-indazole

Refernces

• 1、 -. "HETEROBICYCLIC COMPOUNDS FOR INHIBITING THE ACTIVITY OF SHP2". Paragraph 0577-0579; 0580; 0581. . Retrieved 2020/02/16.
• 2、 -. "SUBSTITUTED QUINOXALINE DERIVATIVES". Page/Page column 244; 345. . Retrieved 2016/12/01.