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

Base Information

• Chemical Name: 2-(4-(difluoromethyl)phenyl)-5-(11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide
• CAS No.: 1621704-24-2
• Molecular Formula: C₃₄H₂₇F₃N₄O₄S
• Molecular Weight: 644.674
• Mol file: 1621704-24-2.mol

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

Chemical Property of 2-(4-(difluoromethyl)phenyl)-5-(11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(4-(difluoromethyl)phenyl)-5-(11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

There total 26 articles about 2-(4-(difluoromethyl)phenyl)-5-(11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)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: 21.0%

2-chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridine (1621705-25-6) + 2-(4-(difluoromethyl)phenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (1621705-30-3) → 2-(4-(difluoromethyl)phenyl)-5-(11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (1621704-24-2)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium carbonate; XPhos; In 1,4-dioxane; water; at 100 ℃; for 2h;

Reference yield:

tert-butyl 4-fluoro-1H-indole-1-carboxylate (129822-45-3) → 2-(4-(difluoromethyl)phenyl)-5-(11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (1621704-24-2)

Guidance literature:

Multi-step reaction with 6 steps

1: n-butyllithium; Triisopropyl borate / tetrahydrofuran; hexane / 0.67 h / -78 °C

2: sodium hydrogencarbonate; bis-triphenylphosphine-palladium(II) chloride / water; 1,4-dioxane / 16 h / 90 °C / Inert atmosphere

3: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

4: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere

5: potassium hydroxide / water; dimethyl sulfoxide / 4 h / 100 °C / Inert atmosphere

6: sodium carbonate; XPhos; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere

With dmap; bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; Triisopropyl borate; sodium hydrogencarbonate; sodium carbonate; N-ethyl-N,N-diisopropylamine; lithium chloride; potassium hydroxide; XPhos; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

(1-(tert-butoxycarbonyl)-4-fluoro-1H-indol-2-yl) boronic acid (1000068-25-6) → 2-(4-(difluoromethyl)phenyl)-5-(11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (1621704-24-2)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydrogencarbonate; bis-triphenylphosphine-palladium(II) chloride / water; 1,4-dioxane / 16 h / 90 °C / Inert atmosphere

2: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

3: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere

4: potassium hydroxide / water; dimethyl sulfoxide / 4 h / 100 °C / Inert atmosphere

5: sodium carbonate; XPhos; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere

With dmap; bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium hydrogencarbonate; sodium carbonate; N-ethyl-N,N-diisopropylamine; lithium chloride; potassium hydroxide; XPhos; In 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

tert-butyl 4-fluoro-1H-indole-1-carboxylate

4-fluoroindole

(1-(tert-butoxycarbonyl)-4-fluoro-1H-indol-2-yl) boronic acid

6-chloro-2-iodopyridine-3-ol