4-[2-(2-chloro-phenyl)-1H-indol-5-yl]-3,N-dimethyl-benzamide

Base Information

• Chemical Name: 4-[2-(2-chloro-phenyl)-1H-indol-5-yl]-3,N-dimethyl-benzamide
• CAS No.: 1279104-66-3
• Molecular Formula: C₂₃H₁₉ClN₂O
• Molecular Weight: 374.87
• Mol file: 1279104-66-3.mol

Synonyms:4-[2-(2-chloro-phenyl)-1H-indol-5-yl]-3,N-dimethyl-benzamide

Chemical Property of 4-[2-(2-chloro-phenyl)-1H-indol-5-yl]-3,N-dimethyl-benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[2-(2-chloro-phenyl)-1H-indol-5-yl]-3,N-dimethyl-benzamide

There total 11 articles about 4-[2-(2-chloro-phenyl)-1H-indol-5-yl]-3,N-dimethyl-benzamide 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: 85.0%

4-[2-(2-chloro-phenyl)-1H-indol-5-yl]-3-methyl-benzoic acid (1279106-98-7) + methylamine hydrochloride (593-51-1) → 4-[2-(2-chloro-phenyl)-1H-indol-5-yl]-3,N-dimethyl-benzamide (1279104-66-3)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

Reference yield:

2-oxoindole (59-48-3) → 4-[2-(2-chloro-phenyl)-1H-indol-5-yl]-3,N-dimethyl-benzamide (1279104-66-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: N-iodo-succinimide; acetic acid / water / 1.5 h

2.1: triethylamine / tetrahydrofuran / 1 h / 20 °C

3.1: ammonium carbonate / N,N-dimethyl-formamide / 3.33 h / 0 - 15 °C

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

5.1: sodium hydrogencarbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / ethanol; toluene / 20 - 60 °C / Inert atmosphere

6.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 20 - 60 °C

7.1: methanol; potassium carbonate / tetrahydrofuran / 5 h / 20 °C

8.1: water; potassium hydroxide / ethanol / 4 h / 100 °C

8.2: pH 2 / Acidic conditions

9.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 4 h / 20 °C

With methanol; N-iodo-succinimide; water; ammonium carbonate; sodium hydrogencarbonate; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

Reference yield:

5-iodo-1,3-dihydro-indol-2-one (193354-13-1) → 4-[2-(2-chloro-phenyl)-1H-indol-5-yl]-3,N-dimethyl-benzamide (1279104-66-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triethylamine / tetrahydrofuran / 1 h / 20 °C

2.1: ammonium carbonate / N,N-dimethyl-formamide / 3.33 h / 0 - 15 °C

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

4.1: sodium hydrogencarbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / ethanol; toluene / 20 - 60 °C / Inert atmosphere

5.1: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 20 - 60 °C

6.1: methanol; potassium carbonate / tetrahydrofuran / 5 h / 20 °C

7.1: water; potassium hydroxide / ethanol / 4 h / 100 °C

7.2: pH 2 / Acidic conditions

8.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 4 h / 20 °C

With methanol; water; ammonium carbonate; sodium hydrogencarbonate; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

4-[2-(2-chloro-phenyl)-1H-indol-5-yl]-3-methyl-benzoic acid

methylamine hydrochloride

4-[2-(2-chloro-phenyl)-1H-indol-5-yl]-3-methyl-benzoic acid methyl ester

2-oxoindole