5-bromo-N-((4'-fluorobiphenyl-4-yl)methyl)-1H-indole-2-sulfonamide

Base Information

• Chemical Name: 5-bromo-N-((4'-fluorobiphenyl-4-yl)methyl)-1H-indole-2-sulfonamide
• CAS No.: 1394431-59-4
• Molecular Formula: C₂₁H₁₆BrFN₂O₂S
• Molecular Weight: 459.339
• Mol file: 1394431-59-4.mol

Synonyms:

Chemical Property of 5-bromo-N-((4'-fluorobiphenyl-4-yl)methyl)-1H-indole-2-sulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-bromo-N-((4'-fluorobiphenyl-4-yl)methyl)-1H-indole-2-sulfonamide

There total 8 articles about 5-bromo-N-((4'-fluorobiphenyl-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:

lithium 5-bromo-1-(phenylsulfonyl)-1H-indole-2-sulfinate (1394431-07-2) → 5-bromo-N-((4'-fluorobiphenyl-4-yl)methyl)-1H-indole-2-sulfonamide (1394431-59-4)

Guidance literature:

Multi-step reaction with 4 steps

1: N-chloro-succinimide / dichloromethane / 2 h / 5 °C

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

3: sodium hydroxide / ethanol / 2 h / Reflux

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

With pyridine; N-chloro-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; sodium hydroxide; In ethanol; dichloromethane; toluene; 4: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2016.08.018

Reference yield:

(4-bromophenyl)hydrazine (589-21-9) → 5-bromo-N-((4'-fluorobiphenyl-4-yl)methyl)-1H-indole-2-sulfonamide (1394431-59-4)

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 / 5 °C

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

7.1: sodium hydroxide / ethanol / 2 h / Reflux

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

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:

ethyl 5-bromoindolecarboxylate (16732-70-0) → 5-bromo-N-((4'-fluorobiphenyl-4-yl)methyl)-1H-indole-2-sulfonamide (1394431-59-4)

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 / 5 °C

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

6.1: sodium hydroxide / ethanol / 2 h / Reflux

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

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:

(4-bromophenyl)hydrazine

ethyl 5-bromoindolecarboxylate

1-Benzenesulfonyl-5-bromo-indole

lithium 5-bromo-1-(phenylsulfonyl)-1H-indole-2-sulfinate