N-(6-fluoro-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[b]thiophene-2-carboxamide

Base Information

• Chemical Name: N-(6-fluoro-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[b]thiophene-2-carboxamide
• CAS No.: 1227210-38-9
• Molecular Formula: C₂₂H₂₃BFNO₃S
• Molecular Weight: 411.305

Synonyms:N-(6-fluoro-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[b]thiophene-2-carboxamide

Chemical Property of N-(6-fluoro-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[b]thiophene-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(6-fluoro-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[b]thiophene-2-carboxamide

There total 4 articles about N-(6-fluoro-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[b]thiophene-2-carboxamide 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:

benzothiophene-2-carboxylic acid chloride (39827-11-7) + 6-fluoro-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1227210-37-8) → N-(6-fluoro-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[b]thiophene-2-carboxamide (1227210-38-9)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

Reference yield:

3-bromo-6-fluoro-2-methyl-aniline (1227210-36-7) → N-(6-fluoro-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[b]thiophene-2-carboxamide (1227210-38-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere

2: pyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

With pyridine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; dichloromethane;

DOI:10.1016/j.bmcl.2015.11.076

Reference yield:

4-Bromo-1-fluoro-2-nitrobenzene (364-73-8) → N-(6-fluoro-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[b]thiophene-2-carboxamide (1227210-38-9)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / -35 °C / Inert atmosphere

2: hydrogenchloride; tin(II) chloride dihdyrate / water; methanol / 2 h / 40 °C

3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 6 h / 100 °C / Inert atmosphere

4: pyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; tin(II) chloride dihdyrate; potassium acetate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

DOI:10.1016/j.bmcl.2015.11.076

upstream raw materials:

benzothiophene-2-carboxylic acid chloride

6-fluoro-2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

4-Bromo-1-fluoro-2-nitrobenzene

1-bromo-4-fluoro-2-methyl-3-nitro-benzene

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