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

Base Information

• Chemical Name: N₅-Allyl-6-chloro-1-methyl-N₂-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide
• CAS No.: 1299482-70-4
• Molecular Formula: C₂₃H₁₈ClF₆N₃O₂
• Molecular Weight: 517.858

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

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

Chemical Property:

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

There total 5 articles about N₅-Allyl-6-chloro-1-methyl-N₂-{2,2,2-trifluoro-1-[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: 52.0%

ethyl 6-chloro-1-methyl-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylate (1299483-29-6) + 1-amino-2-propene (107-11-9,30551-89-4) → N5-Allyl-6-chloro-1-methyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1299482-70-4)

Guidance literature:

With trimethylaluminum; In dichloromethane; toluene; Inert atmosphere; Reflux;

Reference yield:

ethyl-2-chloro-4-amino-benzoate (16017-69-9) → N5-Allyl-6-chloro-1-methyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1299482-70-4)

Guidance literature:

Multi-step reaction with 5 steps

1: iodine / ethanol / 0.75 h / 20 °C

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

3: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / N,N-dimethyl-formamide / 96 h / 20 °C

4: potassium carbonate / acetonitrile / Reflux

5: trimethylaluminum / dichloromethane; toluene / Inert atmosphere; Reflux

With 1,4-diaza-bicyclo[2.2.2]octane; iodine; trimethylaluminum; potassium carbonate; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; palladium diacetate; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

ethyl 4-amino-2-chloro-5-iodobenzoate (1057076-51-3) → N5-Allyl-6-chloro-1-methyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1299482-70-4)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / N,N-dimethyl-formamide / 96 h / 20 °C

3: potassium carbonate / acetonitrile / Reflux

4: trimethylaluminum / dichloromethane; toluene / Inert atmosphere; Reflux

With 1,4-diaza-bicyclo[2.2.2]octane; trimethylaluminum; potassium carbonate; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; palladium diacetate; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

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

ethyl-2-chloro-4-amino-benzoate

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

1-amino-2-propene

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