tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate

Base Information

• Chemical Name: tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate
• CAS No.: 890839-29-9
• Molecular Formula: C18H25BN2O4
• Molecular Weight: 344.218
• Hs Code.: 2934999090
• Mol file: 890839-29-9.mol

Synonyms:tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate;1H-Indazole-1-carboxylic acid, 6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-, 1,1-diMethylethyl ester;1-Boc-6-indazoleboronic acid pinacol ester

Chemical Property of tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate

Chemical Property:

• PSA: 62.58000
• LogP: 3.11870
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

tert-Butyl6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate

There total 4 articles about tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate 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: 46.0%

1,1-dimethylethyl 6-bromo-1H-indazole-1-carboxylate (877264-77-2) + bis(pinacol)diborane (73183-34-3) → 1,1-dimethylethyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate (890839-29-9)

Guidance literature:

With potassium acetate; triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium diacetate; In 1,4-dioxane; at 110 ℃;

Reference yield:

6-bromo-1H-indazole (79762-54-2) + di-tert-butyl dicarbonate (24424-99-5) → 1,1-dimethylethyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate (890839-29-9)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap; triethylamine / acetonitrile / 18 h / 0 - 20 °C

2: triethylamine; potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium diacetate / 1,4-dioxane / 110 °C

With dmap; potassium acetate; triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium diacetate; In 1,4-dioxane; acetonitrile;

Reference yield:

6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (937049-58-6) + di-tert-butyl dicarbonate (24424-99-5) → 1,1-dimethylethyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole-1-carboxylate (890839-29-9)

Guidance literature:

With potassium carbonate; In 1,4-dioxane; at 20 ℃; for 3h;

upstream raw materials:

6-bromo-1H-indazole

di-tert-butyl dicarbonate

1,1-dimethylethyl 6-bromo-1H-indazole-1-carboxylate

bis(pinacol)diborane

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