2-(4-fluorophenyl)-6-(N-(3-hydroxypropyl)methylsulfonamido)-N-methyl-5-(3-(oxazolo[4,5-b]pyridin-2-yl)phenyl)benzofuran-3-carboxamide

Base Information

• Chemical Name: 2-(4-fluorophenyl)-6-(N-(3-hydroxypropyl)methylsulfonamido)-N-methyl-5-(3-(oxazolo[4,5-b]pyridin-2-yl)phenyl)benzofuran-3-carboxamide
• CAS No.: 1333244-00-0
• Molecular Formula: C₃₂H₂₇FN₄O₆S
• Molecular Weight: 614.654
• Mol file: 1333244-00-0.mol

Synonyms:2-(4-fluorophenyl)-6-(N-(3-hydroxypropyl)methylsulfonamido)-N-methyl-5-(3-(oxazolo[4,5-b]pyridin-2-yl)phenyl)benzofuran-3-carboxamide

Chemical Property of 2-(4-fluorophenyl)-6-(N-(3-hydroxypropyl)methylsulfonamido)-N-methyl-5-(3-(oxazolo[4,5-b]pyridin-2-yl)phenyl)benzofuran-3-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(4-fluorophenyl)-6-(N-(3-hydroxypropyl)methylsulfonamido)-N-methyl-5-(3-(oxazolo[4,5-b]pyridin-2-yl)phenyl)benzofuran-3-carboxamide

There total 12 articles about 2-(4-fluorophenyl)-6-(N-(3-hydroxypropyl)methylsulfonamido)-N-methyl-5-(3-(oxazolo[4,5-b]pyridin-2-yl)phenyl)benzofuran-3-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: 30.9%

2-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-oxazolo[4,5-b]pyridine (1029054-27-0) + 5-bromo-2-(4-fluorophenyl)-6-(N-(3-hydroxypropyl)methylsulfonamido)-N-methylbenzofuran-3-carboxamide (1333244-34-0) → 2-(4-fluorophenyl)-6-(N-(3-hydroxypropyl)methylsulfonamido)-N-methyl-5-(3-(oxazolo[4,5-b]pyridin-2-yl)phenyl)benzofuran-3-carboxamide (1333244-00-0)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; acetonitrile; at 100 ℃; for 0.5h; Inert atmosphere; Microwave irradiation;

Reference yield:

5-bromo-2-hydroxylphenylacetic acid methyl ester (220801-66-1) → 2-(4-fluorophenyl)-6-(N-(3-hydroxypropyl)methylsulfonamido)-N-methyl-5-(3-(oxazolo[4,5-b]pyridin-2-yl)phenyl)benzofuran-3-carboxamide (1333244-00-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 1H-imidazole / dichloromethane / 15 h / 0 - 20 °C

2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C

2.2: 1 h / -78 - 0 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C

4.1: hydrogenchloride / water; acetone / 1 h / Reflux

5.1: nitric acid / chloroform / 4 h / 20 °C

6.1: ammonium chloride; iron / water; tetrahydrofuran; methanol / 3 h / Reflux

7.1: pyridine / dichloromethane / 15 h / 0 - 20 °C

8.1: water; lithium hydroxide monohydrate / 1,4-dioxane / 2 h / 80 °C

8.2: pH 6 - 7

9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 3 h / 20 °C

9.2: 8 h / 20 °C

10.1: potassium carbonate / potassium iodide / N,N-dimethyl-formamide / 10 h / 100 °C

11.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; acetonitrile; water / 0.5 h / 100 °C / Inert atmosphere; Microwave irradiation

With pyridine; 1H-imidazole; hydrogenchloride; lithium hydroxide monohydrate; tetrabutyl ammonium fluoride; water; nitric acid; iron; potassium carbonate; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium iodide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; acetonitrile;

Reference yield:

2-Hydroxyphenylacetic acid (614-75-5) → 2-(4-fluorophenyl)-6-(N-(3-hydroxypropyl)methylsulfonamido)-N-methyl-5-(3-(oxazolo[4,5-b]pyridin-2-yl)phenyl)benzofuran-3-carboxamide (1333244-00-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: tetra-N-butylammonium tribromide / 18 h / 20 °C

2.1: 1H-imidazole / dichloromethane / 15 h / 0 - 20 °C

3.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C

3.2: 1 h / -78 - 0 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C

5.1: hydrogenchloride / water; acetone / 1 h / Reflux

6.1: nitric acid / chloroform / 4 h / 20 °C

7.1: ammonium chloride; iron / water; tetrahydrofuran; methanol / 3 h / Reflux

8.1: pyridine / dichloromethane / 15 h / 0 - 20 °C

9.1: water; lithium hydroxide monohydrate / 1,4-dioxane / 2 h / 80 °C

9.2: pH 6 - 7

10.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 3 h / 20 °C

10.2: 8 h / 20 °C

11.1: potassium carbonate / potassium iodide / N,N-dimethyl-formamide / 10 h / 100 °C

12.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; acetonitrile; water / 0.5 h / 100 °C / Inert atmosphere; Microwave irradiation

With pyridine; 1H-imidazole; hydrogenchloride; lithium hydroxide monohydrate; tetrabutyl ammonium fluoride; water; nitric acid; tetra-N-butylammonium tribromide; iron; potassium carbonate; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium iodide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; acetonitrile;

upstream raw materials:

2-Hydroxyphenylacetic acid

5-bromo-2-hydroxylphenylacetic acid methyl ester

2-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-oxazolo[4,5-b]pyridine

5-bromo-2-(4-fluorophenyl)-6-(N-(3-hydroxypropyl)methylsulfonamido)-N-methylbenzofuran-3-carboxamide