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

Base Information

• Chemical Name: 3,6-dichloro-N⁵-(1-cyanocyclopropyl)-1-ethyl-N²-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide
• CAS No.: 1398050-57-1
• Molecular Formula: C₂₅H₁₈Cl₂F₆N₄O₂
• Molecular Weight: 591.34

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

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

Chemical Property:

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

There total 7 articles about 3,6-dichloro-N⁵-(1-cyanocyclopropyl)-1-ethyl-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: 98.0%

6-chloro-N5-(1-cyanocyclopropyl)-1-ethyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1398046-58-6) → 3,6-dichloro-N5-(1-cyanocyclopropyl)-1-ethyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1398050-57-1)

Guidance literature:

With N-chloro-succinimide; In tetrahydrofuran; at 20 ℃; for 48h;

Reference yield:

ethyl 4-amino-2-chloro-5-iodobenzoate (1057076-51-3) → 3,6-dichloro-N5-(1-cyanocyclopropyl)-1-ethyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1398050-57-1)

Guidance literature:

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

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

3.2: 36 h / Inert atmosphere

4.1: boron tribromide / dichloromethane / 3 h / -10 - 20 °C

5.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 - 40 °C

5.2: 16 h / 20 °C

6.1: N-chloro-succinimide / tetrahydrofuran / 48 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; N-chloro-succinimide; oxalyl dichloride; palladium diacetate; boron tribromide; sodium hydride; N,N-dimethyl-formamide; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil;

Reference yield:

ethyl 6-chloro-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylate (1299483-22-9) → 3,6-dichloro-N5-(1-cyanocyclopropyl)-1-ethyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1398050-57-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / Inert atmosphere; Cooling with ice

1.2: 36 h / Inert atmosphere

2.1: boron tribromide / dichloromethane / 3 h / -10 - 20 °C

3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 - 40 °C

3.2: 16 h / 20 °C

4.1: N-chloro-succinimide / tetrahydrofuran / 48 h / 20 °C

With N-chloro-succinimide; oxalyl dichloride; boron tribromide; sodium hydride; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

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

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

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

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

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