Ethyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate

Base Information

• Chemical Name: Ethyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate
• CAS No.: 55899-29-1
• Molecular Formula: C10H9BrN2O2
• Molecular Weight: 269.09466
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID20480502
• Nikkaji Number: J3.660.939G
• Wikidata: Q82315305
• Mol file: 55899-29-1.mol

Synonyms:Ethyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate;55899-29-1;4-Bromo-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester;MFCD20527619;Ethyl4-bromopyrazolo[1,5-a]pyridine-3-carboxylate;SCHEMBL25786093;DTXSID20480502;AMY30431;SB37665;BS-41762;SY268614;CS-0038048;D72630;A870067

Chemical Property of Ethyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate

Chemical Property:

• Melting Point: 68-69 °C(Solv: ligroine (8032-32-4))
• PKA: -0?+-.0.30(Predicted)
• PSA: 43.60000
• Density: 1.60±0.1 g/cm3(Predicted)
• LogP: 2.27350
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 267.98474
• Heavy Atom Count: 15
• Complexity: 250

Purity/Quality:

99%, ^*data from raw suppliers

4-Bromo-pyrazolo[1,5-a]pyridine-3-carboxylicacidethylester 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C2C(=CC=CN2N=C1)Br

Technology Process of Ethyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate

There total 6 articles about Ethyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate 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: 29.0%

3-Bromopyridine (626-55-1,163928-56-1) + propynoic acid ethyl ester (623-47-2) → ethyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate (55899-29-1) + ethyl 6-bromopyrazolo[1,5-a]pyridine-3-carboxylate (55899-30-4)

Guidance literature:

3-Bromopyridine; With mesitylenesulfonylhydroxylamine; In dichloromethane; at 0 ℃; for 2h;

propynoic acid ethyl ester; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1016/j.bmc.2011.11.029

Reference yield: 11.0%

1-amino-3-bromopyridin-1-ium 2,4,6-trimethylbenzenesulfonate (55899-13-3) + propynoic acid ethyl ester (623-47-2) → ethyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate (55899-29-1) + ethyl 6-bromopyrazolo[1,5-a]pyridine-3-carboxylate (55899-30-4)

Guidance literature:

With triethylamine; at 20 ℃; for 0.25h; Flow reactor;

DOI:10.1055/s-0036-1588799

Reference yield: 8.0%

3-Bromopyridine (626-55-1,163928-56-1) + propynoic acid ethyl ester (623-47-2) → ethyl 4-bromopyrazolo[1,5-a]pyridine-3-carboxylate (55899-29-1)

Guidance literature:

3-Bromopyridine; With O-(2,4-dinitrophenyl)hydroxylamine; In acetonitrile; at 40 ℃; for 16h;

propynoic acid ethyl ester; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 20h;

upstream raw materials:

3-Bromopyridine

propynoic acid ethyl ester

1-amino-3-bromopyridin-1-ium 2,4,6-trimethylbenzenesulfonate

ethyl 2-(3-bromopyridin-2-yl)acetate

Downstream raw materials:

N'-((4-bromopyrazolo[1,5-a]pyridin-3-yl)methylene)-N,2-dimethyl-5-nitrobenzenesulfonohydrazide

4-bromopyrazolo[1,5-a]pyridine

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