6-chloro-N⁵-(1-cyanocyclopropyl)-1-(prop-2-yn-1-yl)-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-(prop-2-yn-1-yl)-N²-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide
• CAS No.: 1398047-76-1
• Molecular Formula: C₂₆H₁₇ClF₆N₄O₂
• Molecular Weight: 566.89

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

Chemical Property of 6-chloro-N⁵-(1-cyanocyclopropyl)-1-(prop-2-yn-1-yl)-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-(prop-2-yn-1-yl)-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-(prop-2-yn-1-yl)-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: 50.0%

6-chloro-N5-(1-cyanocyclopropyl)-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1398052-40-8) + propargyl bromide (106-96-7) → 6-chloro-N5-(1-cyanocyclopropyl)-1-(prop-2-yn-1-yl)-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1398047-76-1)

Guidance literature:

6-chloro-N⁵-(1-cyanocyclopropyl)-N²-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 1.5h; Inert atmosphere; Cooling with ice;

propargyl bromide; In N,N-dimethyl-formamide; mineral oil; 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-(prop-2-yn-1-yl)-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1398047-76-1)

Guidance literature:

Multi-step reaction with 3 steps

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

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 / 1.5 h / 0 °C / Inert atmosphere; Cooling with ice

3.2: 16 h / Inert atmosphere

With 4-methyl-morpholine; boron tribromide; 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-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-(prop-2-yn-1-yl)-N2-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-1H-indole-2,5-dicarboxamide (1398047-76-1)

Guidance literature:

Multi-step reaction with 2 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 / 1.5 h / 0 °C / Inert atmosphere; Cooling with ice

2.2: 16 h / Inert atmosphere

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

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

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

propargyl bromide

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