5-Methylpyrazolo[1,5-A]pyridine

Base Information

• Chemical Name: 5-Methylpyrazolo[1,5-A]pyridine
• CAS No.: 104468-72-6
• Molecular Formula: C₈H₈N₂
• Molecular Weight: 132.165
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID30559359
• Wikidata: Q82442054
• Mol file: 104468-72-6.mol

Synonyms:5-METHYLPYRAZOLO[1,5-A]PYRIDINE;104468-72-6;SCHEMBL12489513;DTXSID30559359;AMY30442;MFCD19688318;BS-50479;CS-0437373

Chemical Property of 5-Methylpyrazolo[1,5-A]pyridine

Chemical Property:

• PSA: 17.30000
• LogP: 1.64270
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 132.068748264
• Heavy Atom Count: 10
• Complexity: 124

Purity/Quality:

99%min. ^*data from raw suppliers

5-Methylpyrazolo[1,5-a]pyridine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=CC=NN2C=C1

Technology Process of 5-Methylpyrazolo[1,5-A]pyridine

There total 2 articles about 5-Methylpyrazolo[1,5-A]pyridine 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: 40.7%

(E)-β-phenylthionitroethylene (101933-27-1) + 4-methylpyridinium-N-amino mesitylenesulfonate → 5-methylpyrazolo[1,5-a]pyridine (104468-72-6) + 5-Methyl-3-nitro-pyrazolo[1,5-a]pyridine

Guidance literature:

With triethylamine; In ethanol; for 6h; Heating;

DOI:10.3987/COM-88-4682

Reference yield:

Trimethylboroxine (823-96-1) + 5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) → 5-methylpyrazolo[1,5-a]pyridine (104468-72-6)

Guidance literature:

With palladium diacetate; potassium carbonate; In 1,4-dioxane; water; at 80 ℃; for 1h; Inert atmosphere;

Reference yield:

5-methylpyrazolo[1,5-a]pyridine (104468-72-6) → (1S,3R)-3-acetamido-N-(5-chloro-4-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-yl)pyridin-2-yl)cyclohexanecarboxamide + (1S,3R)-3-acetamido-N-(5-chloro-4-(5-methyl-4, 5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-yl)pyridin-2-yl)cyclohexanecarboxamide

Guidance literature:

Multi-step reaction with 4 steps

1: acetic acid; palladium 10% on activated carbon; hydrogen / methanol / 50 h / 80 °C / 15201 Torr

2: N-iodo-succinimide / acetonitrile / 3 h / 17 - 25 °C

3: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

4: chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); caesium carbonate / 1,4-dioxane; water / 0.5 h / 100 °C / Inert atmosphere

With N-iodo-succinimide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); palladium 10% on activated carbon; hydrogen; caesium carbonate; acetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; water; acetonitrile;

upstream raw materials:

(E)-β-phenylthionitroethylene

Trimethylboroxine

5-bromopyrazolo[1,5-a]pyridine