2-(5-BroMo-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid

Base Information

• Chemical Name: 2-(5-BroMo-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid
• CAS No.: 393509-23-4
• Molecular Formula: C13H11BrFNO2
• Molecular Weight: 312.138
• Hs Code.: 2933990090
• Mol file: 393509-23-4.mol

Synonyms:(+/-)-2-(5-Bromo-7-fluoro-1,2,3-trihydrocyclopenta[2,3-b]indol-3-yl)acetic acid;Cyclopent[b]indole-3-acetic acid,5-bromo-7-fluoro-1,2,3,4-tetrahydro;(+/-)-(5-bromo-7-fluoro-l,2,3.4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid;(+/-)-(5-bromo-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid;

Chemical Property of 2-(5-BroMo-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid

Chemical Property:

• Vapor Pressure: 4.31E-11mmHg at 25°C
• Boiling Point: 506.8±45.0 °C(Predicted)
• PKA: 4.55±0.10(Predicted)
• PSA: 53.09000
• Density: 1.700±0.06 g/cm3(Predicted)
• LogP: 3.57400
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

98%min ^*data from raw suppliers

2-(5-Bromo-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)aceticacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(5-BroMo-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid

There total 12 articles about 2-(5-BroMo-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid 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:

(+/-) 2-(7-fluoro-1,2,3-trihydrocyclopenta[2,3-b]indol-3-yl)acetic acid (393509-22-3) → (5-bromo-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid (393509-23-4)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridinium tribromide; pyridine / 0.75 h / -30 - 20 °C

2: 117 g / AcOH; Zn / 1 h / 20 °C

With pyridine; acetic acid; pyridinium hydrobromide perbromide; zinc;

DOI:10.1021/jm0603668

Reference yield:

(+/-)-(7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid dicyclohexylamine salt → (5-bromo-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid (393509-23-4)

Guidance literature:

(+/-)-(7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid dicyclohexylamine salt; With bromine;

With acetic acid; zinc;

DOI:10.1016/j.tetasy.2005.08.021

Reference yield:

ethyl (2-oxocyclopentyl)acetate (20826-94-2) → (5-bromo-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid (393509-23-4)

Guidance literature:

Multi-step reaction with 5 steps

1: p-TsOH*H₂O / toluene / 20 h / Heating

2: 252 g / nBu₄NCl / Pd(OAc)2 / dimethylformamide / 1 h / 80 °C

3: 92 percent / aq. NaOH / tetrahydrofuran; methanol / 0.25 h / 60 °C

4: pyridinium tribromide; pyridine / 0.75 h / -30 - 20 °C

5: 117 g / AcOH; Zn / 1 h / 20 °C

With pyridine; sodium hydroxide; tetrabutyl-ammonium chloride; toluene-4-sulfonic acid; acetic acid; pyridinium hydrobromide perbromide; zinc; palladium diacetate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm0603668

upstream raw materials:

(+/-) 2-(7-fluoro-1,2,3-trihydrocyclopenta[2,3-b]indol-3-yl)acetic acid

[2-(2-bromo-4-fluoro-phenylimino)-cyclopentyl]-acetic acid ethyl ester

ethyl (2-oxocyclopentyl)acetate

4-fluoro-2-iodoaniline

Downstream raw materials:

[(3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid

[5-bromo-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid methyl ester

[5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid

methyl [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-acetyl-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate

Refernces

• 1、 Sturino, Claudio F.,O'Neill, Gary,Lachance, Nicolas,Boyd, Michael,Berthelette, Carl,Labelle, Marc,Li, Lianhai,Roy, Bruno,Scheigetz, John,Tsou, Nancy,Aubin, Yves,Bateman, Kevin P.,Chauret, Nathalie,Day, Stephen H.,Lévesque, Jean-Fran?ois,Seto, Carmai,Silva, Jose H.,Trimble, Laird A.,Carriere, Marie-Claude,Denis, Danielle,Greig, Gillian,Kargman, Stacia,Lamontagne, Sonia,Mathieu, Marie-Claude,Sawyer, Nicole,Slipetz, Deborah,Abraham, William M.,Jones, Tom,McAuliffe, Malia,Piechuta, Hana,Nicoll-Griffith, Deborah A.,Wang, Zhaoyin,Zamboni, Robert,Young, Robert N.,Metters, Kathleen M.. "Discovery of a potent and selective prostaglandin D2 receptor antagonist, [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4- tetrahydrocyclopenta[b]indol-3-yl]-acetic acid (MK-0524)". . p. 794 - 806. Retrieved 2007/10/03.
• 2、 -. "METHOD OF TREATING ATHEROSCLEROSIS, DYSLIPIDEMIAS AND RELATED CONDITIONS". Page/Page column 29-30. . Retrieved 2010/10/20.