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

Base Information

• Chemical Name: 6-chloro-N⁵-(1-cyanocyclopropyl)-1-cyclopropyl-N²-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide
• CAS No.: 1398050-86-6
• Molecular Formula: C₂₆H₁₉ClF₆N₄O₂
• Molecular Weight: 568.906

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

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

Chemical Property:

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

There total 6 articles about 6-chloro-N⁵-(1-cyanocyclopropyl)-1-cyclopropyl-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: 6.0%

6-chloro-N5-(1-cyanocyclopropyl)-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1398052-40-8) + cyclopropylboronic acid (411235-57-9) → 6-chloro-N5-(1-cyanocyclopropyl)-1-cyclopropyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1398050-86-6)

Guidance literature:

With [2,2]bipyridinyl; copper diacetate; sodium carbonate; In water; N,N-dimethyl-formamide; at 70 ℃; for 16h; Inert atmosphere;

Reference yield:

ethyl 6-chloro-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylate (1299483-22-9) → 6-chloro-N5-(1-cyanocyclopropyl)-1-cyclopropyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1398050-86-6)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: copper diacetate; sodium carbonate; [2,2]bipyridinyl / N,N-dimethyl-formamide; water / 16 h / 70 °C / Inert atmosphere

With 4-methyl-morpholine; [2,2]bipyridinyl; copper diacetate; boron tribromide; sodium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

6-chloro-2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1H-indole-5-carboxylic acid (1299483-23-0) → 6-chloro-N5-(1-cyanocyclopropyl)-1-cyclopropyl-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1398050-86-6)

Guidance literature:

Multi-step reaction with 2 steps

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

2: copper diacetate; sodium carbonate; [2,2]bipyridinyl / N,N-dimethyl-formamide; water / 16 h / 70 °C / Inert atmosphere

With 4-methyl-morpholine; [2,2]bipyridinyl; copper diacetate; sodium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In water; N,N-dimethyl-formamide;

upstream raw materials:

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

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

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

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

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