Ethyl 2-(5-bromopyridin-3-yl)acetate

Base Information

• Chemical Name: Ethyl 2-(5-bromopyridin-3-yl)acetate
• CAS No.: 847375-33-1
• Molecular Formula: C9H10BrNO2
• Molecular Weight: 244.088
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID80709145
• Wikidata: Q82643916
• Mol file: 847375-33-1.mol

Synonyms:Ethyl 2-(5-bromopyridin-3-yl)acetate;847375-33-1;Ethyl 5-Bromopyridine-3-acetate;Ethyl (5-bromopyridin-3-yl)acetate;MFCD12031925;3-Pyridineacetic acid, 5-bromo-, ethyl ester;Ethyl2-(5-bromopyridin-3-yl)acetate;SCHEMBL1922339;DTXSID80709145;NKTQZLOIRUPOCR-UHFFFAOYSA-N;ethyl(5-bromo-3-pyridinyl)acetate;AMY38412;XIB37533;ethyl (5-bromo-3-pyridinyl)acetate;Ethyl 2-(5-bromopyridin-3-yl) acetate;BS-17574;SY238207;CS-0188448;FT-0758436;(5-Bromopyridin-3-yl)acetic acid ethyl ester;(5-bromo-pyridin-3-yl)-acetic acid ethyl ester

Chemical Property of Ethyl 2-(5-bromopyridin-3-yl)acetate

Chemical Property:

• PSA: 39.19000
• LogP: 1.94970
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 242.98949
• Heavy Atom Count: 13
• Complexity: 175

Purity/Quality:

95% ^*data from raw suppliers

Ethyl2-(5-bromopyridin-3-yl)acetate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC1=CC(=CN=C1)Br

Technology Process of Ethyl 2-(5-bromopyridin-3-yl)acetate

There total 6 articles about Ethyl 2-(5-bromopyridin-3-yl)acetate 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: 95.0%

ethanol (64-17-5) + 5-bromo-3-pyridineacetic acid (39891-12-8) → (5-bromo-pyridin-3-yl)-acetic acid ethyl ester (847375-33-1)

Guidance literature:

With sulfuric acid; at 100 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.joc.6b01329

Reference yield: 47.0%

hydrogen ethyl malonate (1071-46-1) + C10H13BBrNO2 → (5-bromo-pyridin-3-yl)-acetic acid ethyl ester (847375-33-1)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); triethylamine; In N,N-dimethyl acetamide; at 20 ℃; for 70h; Sealed tube;

DOI:10.1021/jacs.6b08906

Reference yield: 47.0%

→ (5-bromo-pyridin-3-yl)-acetic acid ethyl ester (847375-33-1)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); triethylamine; In N,N-dimethyl acetamide; at 20 ℃; Sealed tube;

upstream raw materials:

ethanol

5-bromo-3-pyridineacetic acid

(5-bromopyridin-3-yl)methanol

(5-bromo-pyridin-3-yl)-acetonitrile

Downstream raw materials:

(5-{2-[(N-Benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid

(5-{2-[(benzyl-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

Refernces

• 1、 Beck, Hartmut,Jeske, Mario,Thede, Kai,Stoll, Friederike,Flamme, Ingo,Akbaba, Metin,Ergüden, Jens-Kerim,Karig, Gunter,Keldenich, J?rg,Oehme, Felix,Militzer, Hans-Christian,Hartung, Ingo V.,Thuss, Uwe. "Discovery of Molidustat (BAY 85-3934): A Small-Molecule Oral HIF-Prolyl Hydroxylase (HIF-PH) Inhibitor for the Treatment of Renal Anemia". supporting information. p. 988 - 1003. Retrieved 2018/04/19.
• 2、 Fumagalli, Fernando,Da Silva Emery, Flavio. "Charting the Chemical Reactivity Space of 2,3-Substituted Furo[2,3-b]pyridines Synthesized via the Heterocyclization of Pyridine-N-oxide Derivatives". . p. 10339 - 10347. Retrieved 2016/11/17.