1H-INDOLE-2-CARBONYL CHLORIDE,5-BROMO

Base Information

• Chemical Name: 1H-INDOLE-2-CARBONYL CHLORIDE,5-BROMO
• CAS No.: 95538-32-2
• Molecular Formula: C9H5BrClNO
• Molecular Weight: 258.49900
• Hs Code.: 2933990090
• Mol file: 95538-32-2.mol

Synonyms:1H-INDOLE-2-CARBONYL CHLORIDE,5-BROMO;5-bromoindole-2-carboxylic acid chloride;

Chemical Property of 1H-INDOLE-2-CARBONYL CHLORIDE,5-BROMO

Chemical Property:

• PSA: 32.86000
• LogP: 3.30940

Purity/Quality:

98% ^*data from raw suppliers

1H-INDOLE-2-CARBONYLCHLORIDE,5-BROMO 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-INDOLE-2-CARBONYL CHLORIDE,5-BROMO

There total 1 articles about 1H-INDOLE-2-CARBONYL CHLORIDE,5-BROMO 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:

5-bromo-2-indolecarboxylic acid (7254-19-5) → 5-bromo-1H-indole-2-carboxylic acid chloride (95538-32-2)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; In diethyl ether; at 20 ℃; for 2h;

Reference yield:

5-bromo-1H-indole-2-carboxylic acid chloride (95538-32-2) + (3RS)-3-amino-2,3-dihydro-5-(2-fluorophenyl)-1H-1,4-benzodiazepin-2-one (103343-84-6) → 1,3-Dihydro-3-(RS)-(5-Bromoindole-2-carbonylamino)-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one (103343-97-1)

Guidance literature:

With triethylamine; In dichloromethane; Yield given;

DOI:10.1021/jm00120a002

Reference yield:

3-Methylpyridine (108-99-6) + 5-bromo-1H-indole-2-carboxylic acid chloride (95538-32-2) → 1-(5-phenyl-1H-indol-2-yl)-2-(pyridin-3-yl)-ethan-1-one (1278517-86-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 1.5 h / -60 - 0 °C / Inert atmosphere

1.2: 18 h / 0 - 20 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / ethanol; toluene / 20 h / Reflux; Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; ethanol; hexane; toluene; 2.1: Suzuki coupling;

DOI:10.1016/j.bmc.2010.12.032

upstream raw materials:

5-bromo-2-indolecarboxylic acid

Downstream raw materials:

1,3-Dihydro-3-(RS)-(5-Bromoindole-2-carbonylamino)-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one

1-(5-phenyl-1H-indol-2-yl)-2-(pyridin-3-yl)-ethan-1-one

Refernces

• 1、 Dolusic, Eduard,Larrieu, Pierre,Blanc, Sebastien,Sapunaric, Frederic,Norberg, Bernadette,Moineaux, Laurence,Colette, Delphine,Stroobant, Vincent,Pilotte, Luc,Colau, Didier,Ferain, Thierry,Fraser, Graeme,Galeni, Moreno,Frre, Jean-Marie,Masereel, Bernard,Van Den Eynde, Benoit,Wouters, Johan,Frederick, Raphael. "Indol-2-yl ethanones as novel indoleamine 2,3-dioxygenase (IDO) inhibitors". experimental part. p. 1550 - 1561. Retrieved 2011/03/22.