ethyl 5-chloro-[1,2,4]triazolo[4,3-a]pyrimidine-7-carboxylat

Base Information

• Chemical Name: ethyl 5-chloro-[1,2,4]triazolo[4,3-a]pyrimidine-7-carboxylat
• CAS No.: 916325-84-3
• Molecular Formula: C8H6BrN3O2
• Molecular Weight: 256.059
• Hs Code.: 2933990090
• Mol file: 916325-84-3.mol

Synonyms:Methyl 5-bromo-2H-pyrazolo[3,4-b]pyridine-3-carboxylate;Methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate;TC-072663;

Chemical Property of ethyl 5-chloro-[1,2,4]triazolo[4,3-a]pyrimidine-7-carboxylat

Chemical Property:

• Refractive Index: 1.689
• Boiling Point: 394.9±37.0 °C(Predicted)
• PKA: 6.59±0.40(Predicted)
• PSA: 69.38000
• Density: 1.798 g/cm³
• LogP: 0.95440
• Storage Temp.: 2-8°C

Purity/Quality:

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

Methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 5-Bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate is used in preparation of Indazole containing Macrocycles for treating disorders characterized by the activation of Wnt pathway signaling.

Technology Process of ethyl 5-chloro-[1,2,4]triazolo[4,3-a]pyrimidine-7-carboxylat

There total 9 articles about ethyl 5-chloro-[1,2,4]triazolo[4,3-a]pyrimidine-7-carboxylat 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: 47.0%

pyrazolo[3,4-b]pyridine-3-carboxylic acid methyl ester (916325-83-2) → methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (916325-84-3)

Guidance literature:

With bromine; sodium acetate; acetic acid; at 115 ℃; Sealed tube;

Reference yield:

methanol (67-56-1) + 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid (916325-85-4) → methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (916325-84-3)

Guidance literature:

With sulfuric acid; at 70 ℃; for 20h; Large scale;

Reference yield:

3-acetyl-2-chloropyridine (55676-21-6) → methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (916325-84-3)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrazine hydrate / butan-1-ol / Reflux

2: sodium hydroxide; water; potassium permanganate / 80 - 90 °C

3: sulfuric acid / 6 h / Reflux; Inert atmosphere

4: sodium acetate; bromine; acetic acid / 120 °C / in a sealed tube

With potassium permanganate; sulfuric acid; water; bromine; sodium acetate; hydrazine hydrate; acetic acid; sodium hydroxide; In butan-1-ol;

upstream raw materials:

pyrazolo[3,4-b]pyridine-3-carboxylic acid methyl ester

3-acetyl-2-chloropyridine

2-chloropyridine

3-methyl-1H-pyrazolo[3,4b]pyridine

Downstream raw materials:

5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid

5-bromo-1methyl-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid methyl ester

1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde

Refernces

• 1、 -. "3-(3H-IMIDAZO[4,5-B]PYRIDIN-2-YL)-1H-PYRAZOLO[3,4-B]PYRIDINE AND THERAPEUTIC USES THEREOF". Paragraph 1060. . Retrieved 2016/04/20.
• 2、 -. "ALKYNYL ALCOHOLS AND METHODS OF USE". Page/Page column 133. . Retrieved 2015/03/13.