3-(4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide

Base Information

Chemical Name:3-(4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide
CAS No.:1423160-78-4
Molecular Formula:C₂₁H₁₇ClN₆O₂S₂
Molecular Weight:484.99
Hs Code.:

Synonyms:3-(4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide

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Chemical Property of 3-(4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide

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Technology Process of 3-(4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide

There total 17 articles about 3-(4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide 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: 44.1%

: N-(2,4-dimethoxybenzyl)-1-methyl-3-(2-(1-methyl-1H-pyrazol-5-yl)-4-(trifluoromethyl)phenyl)-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide

: 1423160-78-4
3-(4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide

Guidance literature:: With potassium carbonate; In 1,4-dioxane; methanol; for 0.75h;

Reference yield:

: 52415-29-9
6-bromo-1H-indole

: 1423160-78-4
3-(4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydride / tetrahydrofuran / 0.33 h / 10 °C / Inert atmosphere

1.2: 0.27 h / 10 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / 0.25 h / Inert atmosphere; Cooling with acetone-dry ice

2.2: Inert atmosphere; Cooling with acetone-dry ice

2.3: 0.33 h / Cooling with ice

3.1: N-Bromosuccinimide / dichloromethane

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / Inert atmosphere; Cooling with acetone-dry ice

4.2: Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

6.1: potassium phosphate; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II) / 1,4-dioxane; water / 0.33 h / 90 °C / Inert atmosphere; Sealed tube

7.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / Inert atmosphere; Cooling with ice

7.2: Inert atmosphere

8.1: potassium carbonate / 1,4-dioxane; methanol / 0.75 h

With potassium phosphate; N-Bromosuccinimide; n-butyllithium; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

Reference yield:

: 1423161-84-5
3-bromo-1-methyl-1H-indole-6-sulfonyl chloride

: 1423160-78-4
3-(4-chloro-2-(1-methyl-1H-pyrazol-5-yl)phenyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -78 °C

1.2: 2 h / -78 °C

2.1: potassium phosphate; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II) / 1,4-dioxane; water / 0.33 h / 90 °C / Sealed tube; Microwave irradiation; Heating

3.1: acetyl chloride; methanol / dichloromethane / 1 h

With methanol; potassium phosphate; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); acetyl chloride; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;
DOI:10.1021/acsmedchemlett.6b00243