5-chloro-N-((4'-(methylsulfonyl)biphenyl-4-yl)methyl)-1H-indole-2-sulfonamide

Base Information

• Chemical Name: 5-chloro-N-((4'-(methylsulfonyl)biphenyl-4-yl)methyl)-1H-indole-2-sulfonamide
• CAS No.: 1394431-80-1
• Molecular Formula: C₂₂H₁₉ClN₂O₄S₂
• Molecular Weight: 474.989

Synonyms:5-chloro-N-((4'-(methylsulfonyl)biphenyl-4-yl)methyl)-1H-indole-2-sulfonamide

Chemical Property of 5-chloro-N-((4'-(methylsulfonyl)biphenyl-4-yl)methyl)-1H-indole-2-sulfonamide

Chemical Property:

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Technology Process of 5-chloro-N-((4'-(methylsulfonyl)biphenyl-4-yl)methyl)-1H-indole-2-sulfonamide

There total 9 articles about 5-chloro-N-((4'-(methylsulfonyl)biphenyl-4-yl)methyl)-1H-indole-2-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:

N-(4-bromobenzyl)-5-chloro-1H-indole-2-sulfonamide + 4-methanesulphonylphenylboronic acid (149104-88-1) → 5-chloro-N-((4'-(methylsulfonyl)biphenyl-4-yl)methyl)-1H-indole-2-sulfonamide (1394431-80-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In ethanol; toluene; for 3h; Reflux; Inert atmosphere;

DOI:10.1016/j.bmcl.2016.08.018

Reference yield:

N-4-chlorophenylhydrazine (1073-69-4) → 5-chloro-N-((4'-(methylsulfonyl)biphenyl-4-yl)methyl)-1H-indole-2-sulfonamide (1394431-80-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: toluene-4-sulfonic acid / 20 h / Reflux

2.1: sodium hydroxide / ethanol / 40 °C

2.2: 0.42 h / 250 °C / Microwave irradiation

3.1: sodium hydride / N,N-dimethyl-formamide / 18 h / 20 °C

4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -70 °C / Inert atmosphere

4.2: 2.25 h / -70 - 20 °C / Inert atmosphere

5.1: N-chloro-succinimide / dichloromethane / 2 h / 0 - 20 °C

6.1: pyridine / dichloromethane / 18 h / 0 - 20 °C

7.1: sodium hydroxide / ethanol / Reflux

8.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / ethanol; toluene / 3 h / Reflux; Inert atmosphere

With pyridine; N-chloro-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium hydride; sodium carbonate; toluene-4-sulfonic acid; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 8.1: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2016.08.018

Reference yield:

5-chloro-indole-2-carboxylic acid ethyl ester (4792-67-0) → 5-chloro-N-((4'-(methylsulfonyl)biphenyl-4-yl)methyl)-1H-indole-2-sulfonamide (1394431-80-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydroxide / ethanol / 40 °C

1.2: 0.42 h / 250 °C / Microwave irradiation

2.1: sodium hydride / N,N-dimethyl-formamide / 18 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -70 °C / Inert atmosphere

3.2: 2.25 h / -70 - 20 °C / Inert atmosphere

4.1: N-chloro-succinimide / dichloromethane / 2 h / 0 - 20 °C

5.1: pyridine / dichloromethane / 18 h / 0 - 20 °C

6.1: sodium hydroxide / ethanol / Reflux

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / ethanol; toluene / 3 h / Reflux; Inert atmosphere

With pyridine; N-chloro-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium hydride; sodium carbonate; sodium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 7.1: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2016.08.018

upstream raw materials:

N-4-chlorophenylhydrazine

5-chloro-indole-2-carboxylic acid ethyl ester

5-chloro-1H-indole

5-chloro-1-(phenylsulfonyl)-1H-indole

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