N-{[(3R)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-4-(1H-indol-5-yl)-N-(1-methylethyl)benzamide

Base Information

• Chemical Name: N-{[(3R)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-4-(1H-indol-5-yl)-N-(1-methylethyl)benzamide
• CAS No.: 1426095-29-5
• Molecular Formula: C₂₇H₃₁N₃O₂
• Molecular Weight: 429.562
• Mol file: 1426095-29-5.mol

Synonyms:N-{[(3R)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-4-(1H-indol-5-yl)-N-(1-methylethyl)benzamide

Chemical Property of N-{[(3R)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-4-(1H-indol-5-yl)-N-(1-methylethyl)benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{[(3R)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-4-(1H-indol-5-yl)-N-(1-methylethyl)benzamide

There total 10 articles about N-{[(3R)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-4-(1H-indol-5-yl)-N-(1-methylethyl)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:

4-bromo-N-{[(3R)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-N-(1-methylethyl)benzamide (1426095-96-6) + 1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (777061-36-6) → N-{[(3R)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-4-(1H-indol-5-yl)-N-(1-methylethyl)benzamide (1426095-29-5)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 80 ℃; Inert atmosphere;

Reference yield:

1,1-dimethylethyl (3S)-3-(aminomethyl)-1-pyrrolidinecarboxylate (199175-10-5) → N-{[(3R)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-4-(1H-indol-5-yl)-N-(1-methylethyl)benzamide (1426095-29-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 4 h / 20 °C

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

3.1: hydrogenchloride / methanol / 20 °C

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 °C

4.2: 20 °C

5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 80 °C / Inert atmosphere

With hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tris(acetoxy)borohydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; dichloromethane; water;

Reference yield:

5-bromo-indole-1-carboxylic acid tert-butyl ester (182344-70-3) → N-{[(3R)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-4-(1H-indol-5-yl)-N-(1-methylethyl)benzamide (1426095-29-5)

Guidance literature:

Multi-step reaction with 2 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium diacetate; triethylamine / 110 °C / Inert atmosphere

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium diacetate; potassium carbonate; triethylamine; In 1,4-dioxane; water;

upstream raw materials:

1,1-dimethylethyl (3S)-3-(aminomethyl)-1-pyrrolidinecarboxylate

4-bromo-N-{[(3R)-1-cyclopropylcarbonyl-3-pyrrolidinyl]methyl}-N-(1-methylethyl)benzamide

1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

5-bromo-indole-1-carboxylic acid tert-butyl ester