(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethanesulfonamido)benzofuran-5-yl)boronic acid

Base Information

• Chemical Name: (2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethanesulfonamido)benzofuran-5-yl)boronic acid
• CAS No.: 1621705-60-9
• Molecular Formula: C₁₈H₁₈BFN₂O₆S
• Molecular Weight: 420.226
• Mol file: 1621705-60-9.mol

Synonyms:(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethanesulfonamido)benzofuran-5-yl)boronic acid

Chemical Property of (2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethanesulfonamido)benzofuran-5-yl)boronic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethanesulfonamido)benzofuran-5-yl)boronic acid

There total 11 articles about (2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethanesulfonamido)benzofuran-5-yl)boronic acid 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:

5-bromo-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzo furan-3-carboxamide (1333225-20-9) → (2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethanesulfonamido)benzofuran-5-yl)boronic acid (1621705-60-9) + C18H17FN2O4S

Guidance literature:

With tetrahydroxydiboron; chloro[(tricyclohexylphosphine)-2-(2'-aminobiphenyl)]palladium(II) second generation; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine; In methanol; at 60 - 65 ℃; for 1h; Temperature; Concentration; Solvent; Overall yield = 27.54 kg; Inert atmosphere; Large scale;

DOI:10.1021/acs.oprd.5b00405

Reference yield:

5-bromo-2-hydroxylphenylacetic acid methyl ester (220801-66-1) → (2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethanesulfonamido)benzofuran-5-yl)boronic acid (1621705-60-9) + C18H17FN2O4S

Guidance literature:

Multi-step reaction with 10 steps

1.1: 1H-imidazole / dichloromethane / 8 h / 20 - 25 °C / Inert atmosphere; Large scale

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 4 h / -70 - -50 °C / Inert atmosphere; Large scale

2.2: 1 h / -70 - -50 °C / Inert atmosphere; Large scale

3.1: hydrogenchloride / acetone; water / 22 h / 20 - 45 °C / Inert atmosphere; Large scale

4.1: nitric acid; trifluoroacetic acid / 1 h / 40 - 55 °C / Inert atmosphere; Large scale

5.1: ammonium chloride; iron / methanol; tetrahydrofuran; water / 2 h / 65 - 70 °C / Inert atmosphere; Large scale

6.1: pyridine / dichloromethane / 22 h / 30 °C / Inert atmosphere; Large scale

7.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 30 - 40 °C / Inert atmosphere; Large scale

8.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 6 h / Reflux; Inert atmosphere; Large scale

9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 7 h / 25 - 30 °C / Inert atmosphere; Large scale

10.1: tetrahydroxydiboron; tricyclohexylphosphine; N-ethyl-N,N-diisopropylamine; chloro[(tricyclohexylphosphine)-2-(2'-aminobiphenyl)]palladium(II) second generation / methanol / 1 h / 60 - 65 °C / Inert atmosphere; Large scale

With pyridine; 1H-imidazole; hydrogenchloride; tetrahydroxydiboron; lithium hydroxide monohydrate; chloro[(tricyclohexylphosphine)-2-(2'-aminobiphenyl)]palladium(II) second generation; water; nitric acid; iron; potassium carbonate; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hexamethyldisilazane; tricyclohexylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; 10.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.oprd.5b00405

Reference yield:

methyl 5-bromo-2-(4-fluorophenyl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxylate (1333225-35-6) → (2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethanesulfonamido)benzofuran-5-yl)boronic acid (1621705-60-9) + C18H17FN2O4S

Guidance literature:

Multi-step reaction with 3 steps

1: lithium hydroxide monohydrate; water / tetrahydrofuran / 6 h / Reflux; Inert atmosphere; Large scale

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 7 h / 25 - 30 °C / Inert atmosphere; Large scale

3: tetrahydroxydiboron; tricyclohexylphosphine; N-ethyl-N,N-diisopropylamine; chloro[(tricyclohexylphosphine)-2-(2'-aminobiphenyl)]palladium(II) second generation / methanol / 1 h / 60 - 65 °C / Inert atmosphere; Large scale

With tetrahydroxydiboron; lithium hydroxide monohydrate; chloro[(tricyclohexylphosphine)-2-(2'-aminobiphenyl)]palladium(II) second generation; water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 3: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.oprd.5b00405

upstream raw materials:

methyl 5-bromo-2-(4-fluorophenyl)benzofuran-3-carboxylate

methyl 5-bromo-2-(4-fluorophenyl)-6-nitrobenzofuran-3-carboxylate

methyl 6-amino-5-bromo-2-(4-fluorophenyl)benzofuran-3-carboxylate

methyl 5-bromo-2-(4-fluorophenyl)-6-(methanesulfonamido)benzofuran-3-carboxylate

Downstream raw materials:

5-(11-fluoro-6-(2-hydroxyethyl)-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

2-(4-fluorophenyl)-5-(11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-2-yl)-N-methyl-6-(N-methylmethanesulfonamido)-1-benzofuran-3-carboxamide

5-(6-chloro-5-(1-(hydroxymethyl)cyclopropyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

5-(11-fluoro-5,6-dihydropyridazino[4’,3‘:3,4]pyrido[1,2-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide