6-chloro-N⁵-(2,2-difluoroethyl)-1-ethyl-N²-{2,2,2-trifluoro-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide

Base Information

• Chemical Name: 6-chloro-N⁵-(2,2-difluoroethyl)-1-ethyl-N²-{2,2,2-trifluoro-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide
• CAS No.: 1421279-66-4
• Molecular Formula: C₂₃H₁₇ClF₉N₃O₂
• Molecular Weight: 573.846

Synonyms:6-chloro-N⁵-(2,2-difluoroethyl)-1-ethyl-N²-{2,2,2-trifluoro-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide

Chemical Property of 6-chloro-N⁵-(2,2-difluoroethyl)-1-ethyl-N²-{2,2,2-trifluoro-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide

Chemical Property:

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Technology Process of 6-chloro-N⁵-(2,2-difluoroethyl)-1-ethyl-N²-{2,2,2-trifluoro-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide

There total 7 articles about 6-chloro-N⁵-(2,2-difluoroethyl)-1-ethyl-N²-{2,2,2-trifluoro-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide 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: 81.0%

2,2-difluorethylamine (430-67-1) + ethyl 6-chloro-1-ethyl-2-({2,2,2-trifluoro-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylate (1398051-47-2) → 6-chloro-N5-(2,2-difluoroethyl)-1-ethyl-N2-{2,2,2-trifluoro-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1421279-66-4)

Guidance literature:

With trimethylaluminum; In dichloromethane; at 20 ℃; for 16.5h; Inert atmosphere; Reflux;

Reference yield:

ethyl 4-amino-2-chloro-5-iodobenzoate (1057076-51-3) → 6-chloro-N5-(2,2-difluoroethyl)-1-ethyl-N2-{2,2,2-trifluoro-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1421279-66-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: palladium diacetate; 1,4-diaza-bicyclo[2.2.2]octane / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere

2.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 4-methyl-morpholine / N,N-dimethyl-formamide / 16 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 °C / Inert atmosphere; Cooling with ice

3.2: 36 h / Inert atmosphere

4.1: trimethylaluminum / dichloromethane / 16.5 h / 20 °C / Inert atmosphere; Reflux

With 4-methyl-morpholine; 1,4-diaza-bicyclo[2.2.2]octane; trimethylaluminum; palladium diacetate; sodium hydride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide; mineral oil;

Reference yield:

6-chloro-5-(ethoxycarbonyl)-1H-indole-2-carboxylic acid (1299483-21-8) → 6-chloro-N5-(2,2-difluoroethyl)-1-ethyl-N2-{2,2,2-trifluoro-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1421279-66-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 4-methyl-morpholine / N,N-dimethyl-formamide / 16 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 °C / Inert atmosphere; Cooling with ice

2.2: 36 h / Inert atmosphere

3.1: trimethylaluminum / dichloromethane / 16.5 h / 20 °C / Inert atmosphere; Reflux

With 4-methyl-morpholine; trimethylaluminum; sodium hydride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In dichloromethane; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

ethyl 4-amino-2-chloro-5-iodobenzoate

2,2-difluorethylamine

ethyl 6-chloro-1-ethyl-2-({2,2,2-trifluoro-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylate

6-chloro-5-(ethoxycarbonyl)-1H-indole-2-carboxylic acid

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