1H-Pyrrole-3-carboxylic acid, 5-(2-fluorophenyl)-, ethyl ester

Base Information

• Chemical Name: 1H-Pyrrole-3-carboxylic acid, 5-(2-fluorophenyl)-, ethyl ester
• CAS No.: 881674-06-2
• Molecular Formula: C13H12FNO2
• Molecular Weight: 233.242
• Mol file: 881674-06-2.mol

Synonyms:5-(2-Fluorophenyl)-1H-pyrrole-3-carboxylic acid ethyl ester;

Chemical Property of 1H-Pyrrole-3-carboxylic acid, 5-(2-fluorophenyl)-, ethyl ester

Chemical Property:

• Boiling Point: 424.7±35.0 °C(Predicted)
• PKA: 14.68±0.50(Predicted)
• PSA: 42.09000
• Density: 1.217±0.06 g/cm3 (20 oC 760 Torr)
• LogP: 2.99750

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Pyrrole-3-carboxylic acid, 5-(2-fluorophenyl)-, ethyl ester

There total 5 articles about 1H-Pyrrole-3-carboxylic acid, 5-(2-fluorophenyl)-, ethyl 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: 30.0%

ethyl 2-cyano-4-(2-fluorophenyl)-4-oxobutanoate (881673-98-9) → 5-(2-fluorophenyl)-1H-pyrrole-3-carboxylic acid ethyl ester (881674-06-2)

Guidance literature:

ethyl 2-cyano-4-(2-fluorophenyl)-4-oxobutanoate; With hydrogenchloride; In tetrahydrofuran; for 3h; Cooling with ice;

With palladium 10% on activated carbon; hydrogen; In ethanol; for 24h;

Reference yield: 18.0%

ethyl 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate (881674-01-7) → 5-(2-fluorophenyl)-1H-pyrrole-3-carboxylic acid ethyl ester (881674-06-2)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In ethanol; at 20 ℃; for 96h;

Reference yield:

2-bromo-2'-fluoroacetophenone (655-15-2) → 5-(2-fluorophenyl)-1H-pyrrole-3-carboxylic acid ethyl ester (881674-06-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / 0.75 h / 40 - 45 °C

1.2: 18 h / 20 °C

2.1: hydrogenchloride / tetrahydrofuran / 20 °C / Cooling with ice

3.1: palladium 10% on activated carbon; hydrogen / ethanol / 24 h / 20 °C

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; potassium carbonate; In tetrahydrofuran; ethanol;

DOI:10.1021/jm300318t

upstream raw materials:

ethyl 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carboxylate

ethyl 2-cyano-4-(2-fluorophenyl)-4-oxobutanoate

2-bromo-2'-fluoroacetophenone

ethyl 2-cyanoacetate

Downstream raw materials:

(5-(2-fluorophenyl)-1H-pyrrol-3-yl)methanol

5-(2-fluorophenyl)-1H-pyrrole-3-carboxaldehyde

1-[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrole-3-yl]-N-methylmethylamine fumaric acid salt

1-(5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-yl)-N-methylmethanamine

Refernces

• 1、 -. "Preparation method of drug for treating gastric acid related diseases". Paragraph 0040; 0041. . Retrieved 2016/10/10.
• 2、 Arikawa, Yasuyoshi,Nishida, Haruyuki,Kurasawa, Osamu,Hasuoka, Atsushi,Hirase, Keizo,Inatomi, Nobuhiro,Hori, Yasunobu,Matsukawa, Jun,Imanishi, Akio,Kondo, Mitsuyo,Tarui, Naoki,Hamada, Teruki,Takagi, Terufumi,Takeuchi, Toshiyuki,Kajino, Masahiro. "Discovery of a novel pyrrole derivative 1-[5-(2-fluorophenyl)-1-(pyridin-3- ylsulfonyl)-1 H -pyrrol-3-yl]- n -methylmethanamine fumarate (tak-438) as a Potassium-Competitive Acid Blocker (P-CAB)". experimental part. p. 4446 - 4456. Retrieved 2012/07/28.