6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one

Base Information

• Chemical Name: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one
• CAS No.: 893441-85-5
• Molecular Formula: C14H18BNO3
• Molecular Weight: 259.113
• Hs Code.: 2934999090
• Mol file: 893441-85-5.mol

Synonyms:6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one;Oxindole-6-boronic acid, pinacol ester;2-Oxoindoline-6-boronic Acid Pinacol Ester;6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indol-2-one

Chemical Property of 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one

Chemical Property:

• PSA: 47.56000
• Density: 1.16±0.1 g/cm3 (20 ºC 760 Torr)
• LogP: 1.61840
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one is useful for preparation of imidazopyridazines as therapeutic kinase inhibitors.

Technology Process of 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one

There total 5 articles about 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one 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: 75.0%

6-bromo-2,3-dihydro-1H-indole-2-one (99365-40-9) + bis(pinacol)diborane (73183-34-3) → 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline-2-one (893441-85-5)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,2-dimethoxyethane; at 80 ℃;

Reference yield:

1,4-dibromo-2-nitrobenzene (3460-18-2) → 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline-2-one (893441-85-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.17 h / 90 °C

1.2: 2 h / 90 °C

2.1: lithium chloride / dimethyl sulfoxide / 20 h / 100 °C

3.1: acetic acid; iron / 1 h / 110 °C

4.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dimethyl sulfoxide / 18 h / 90 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium tert-butylate; potassium acetate; iron; acetic acid; lithium chloride; In dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

C9H6BrNO6 (1098855-11-8) → 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline-2-one (893441-85-5)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid; iron / 1 h / 110 °C

2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dimethyl sulfoxide / 18 h / 90 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; iron; acetic acid; In dimethyl sulfoxide;

upstream raw materials:

6-bromo-2,3-dihydro-1H-indole-2-one

bis(pinacol)diborane

1,4-dibromo-2-nitrobenzene

C₉H₆BrNO₆

Downstream raw materials:

(S)-tert-butyl 1-(1-amino-1-oxo-3-(4-(2-oxoindolin-6-yl)phenyl)propan-2-ylcarbamoyl)cyclohexylcarbamate

6-(6-(3-(3-fluorophenyl)morpholino)imidazo[1,2-b]pyridazin-3-yl)indolin-2-one