3-Pyridinecarboxylic acid, 5-broMo-6-chloro-, ethyl ester

Base Information

• Chemical Name: 3-Pyridinecarboxylic acid, 5-broMo-6-chloro-, ethyl ester
• CAS No.: 952063-30-8
• Molecular Formula: C₈H₇BrClNO₂
• Molecular Weight: 264.506
• Hs Code.: 2933399090
• Mol file: 952063-30-8.mol

Synonyms:3-Pyridinecarboxylic acid, 5-broMo-6-chloro-, ethyl ester;ethyl 5-broMo-6-chloronicotinate;ethyl 5-bromo-6-chloropyridine-3-carboxylate;3-PYRIDINECARBONYL CHLORIDE, 5-BROMO-6-CHLORO-, ETYHL ESTER

Chemical Property of 3-Pyridinecarboxylic acid, 5-broMo-6-chloro-, ethyl ester

Chemical Property:

• PSA: 39.19000
• LogP: 2.67420

Purity/Quality:

99% ^*data from raw suppliers

3-PYRIDINECARBONYLCHLORIDE,5-BROMO-6-CHLORO-,ETYHLESTER 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Pyridinecarboxylic acid, 5-broMo-6-chloro-, ethyl ester

There total 2 articles about 3-Pyridinecarboxylic acid, 5-broMo-6-chloro-, 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: 78.0%

ethanol (64-17-5) + 5-bromo-6-chloronicotinic acid (29241-62-1) → ethyl 5-bromo-6-chloronicotinate (952063-30-8)

Guidance literature:

ethanol; 5-bromo-6-chloronicotinic acid; With sulfuric acid; In water; for 5h; Heating / reflux;

With sodium hydroxide; In dichloromethane; water;

Reference yield:

3-bromo-5-(ethoxycarbonyl)pyridine-1-oxide (279248-42-9) → ethyl 5-bromo-6-chloronicotinate (952063-30-8) + ethyl 5-bromo-2-chloronicotinate (1214332-67-8)

Guidance literature:

With oxalyl dichloride; triethylamine; In dichloromethane; at -70 ℃; for 0.5h; Overall yield = 87.9 %; Overall yield = 465 mg; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.5b01057

Reference yield:

ethyl 5-bromo-6-chloronicotinate (952063-30-8) → ethyl 6-[4-(anilinocarbonyl)piperazin-1-yl]-5-cyanonicotinate

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / ethanol / 0.17 h / 120 °C / Microwave irradiation

2.1: acetonitrile / 16 h / 20 °C

3.1: N,N,N,N,-tetramethylethylenediamine; 1,5-bis-(diphenylphosphino)pentane; palladium diacetate / toluene / 0 - 20 °C / Inert atmosphere

3.2: 16 h / 120 °C / Inert atmosphere

With N,N,N,N,-tetramethylethylenediamine; 1,5-bis-(diphenylphosphino)pentane; palladium diacetate; triethylamine; In ethanol; toluene; acetonitrile;

DOI:10.1016/j.bmcl.2011.03.088

upstream raw materials:

ethanol

5-bromo-6-chloronicotinic acid

3-bromo-5-(ethoxycarbonyl)pyridine-1-oxide

Refernces

• 1、 Chen, Ying,Huang, Jinkun,Hwang, Tsang-Lin,Chen, Maosheng J.,Tedrow, Jason S.,Farrell, Robert P.,Bio, Matthew M.,Cui, Sheng. "Highly Regioselective Halogenation of Pyridine N -Oxide: Practical Access to 2-Halo-Substituted Pyridines". supporting information. p. 2948 - 2951. Retrieved 2015/06/30.
• 2、 -. "NEW PYRIDINE ANALOGUES II". Page/Page column 28. . Retrieved 2008/06/13.