2-{5-[4-(5-bromo-thiophen-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 2-{5-[4-(5-bromo-thiophen-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 1256385-48-4
• Molecular Formula: C₂₂H₂₄BrN₃O₂S
• Molecular Weight: 474.421
• Mol file: 1256385-48-4.mol

Synonyms:2-{5-[4-(5-bromo-thiophen-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of 2-{5-[4-(5-bromo-thiophen-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{5-[4-(5-bromo-thiophen-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 1 articles about 2-{5-[4-(5-bromo-thiophen-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester 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: 98.0%

2,5-dibromothiophen (3141-27-3) + (S)-tert-butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (1007882-12-3) → 2-{5-[4-(5-bromo-thiophen-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester (1256385-48-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,2-dimethoxyethane; at 90 ℃; for 8h;

DOI:10.1021/jm401499g

Reference yield: 72.0%

2-{5-[4-(5-bromo-thiophen-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester (1256385-48-4) + bis(pinacol)diborane (73183-34-3) → 2-(5-{4-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)thiophen-2-yl]-phenyl}1H-imidazol-2-yl)pyrrolidine-1-carboxylic acid tert-butyl ester (1256385-49-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; In 1,4-dioxane; at 90 ℃; for 16h;

DOI:10.1021/jm401499g

Reference yield:

2-{5-[4-(5-bromo-thiophen-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester (1256385-48-4) → (S)-tert-butyl 2-(5-(4-(5-(2-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-1Hbenzo[d]imidazol-6-yl)thiophen-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate trifluoroacetate salt

Guidance literature:

Multi-step reaction with 2 steps

1: potassium acetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 16 h / 90 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / 1,2-dimethoxyethane / 0.5 h / 110 °C / Microwave irradiation

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; potassium carbonate; In 1,4-dioxane; 1,2-dimethoxyethane; 2: |Suzuki Coupling;

DOI:10.1021/jm401499g

upstream raw materials:

2,5-dibromothiophen

(S)-tert-butyl 2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

Downstream raw materials:

2-(5-{4-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)thiophen-2-yl]-phenyl}1H-imidazol-2-yl)pyrrolidine-1-carboxylic acid tert-butyl ester