tert-butyl 3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate
• CAS No.: 1034474-40-2
• Molecular Formula: C₂₅H₁₉Cl₂N₇O₃
• Molecular Weight: 536.377
• Mol file: 1034474-40-2.mol

Synonyms:tert-butyl 3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

Chemical Property of tert-butyl 3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

There total 13 articles about tert-butyl 3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-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: 31.0%

3-chloro-5-[(5-chloro-1H-1,2,3-benzotriazol-4-yl)oxy]benzonitrile (1034474-39-9) + 3-bromomethylpyrazolo[3,4-b]pyridine-1-carboxylic acid tert-butyl ester (174180-76-8) → tert-butyl 3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (1034474-40-2)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jm2010173

Reference yield:

2-(3-bromo-5-chlorophenoxy)-1-chloro-3-nitrobenzene (1034474-41-3) → tert-butyl 3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (1034474-40-2)

Guidance literature:

Multi-step reaction with 5 steps

1: N,N,N-trimethylhydrazinium iodide; potassium carbonate; copper(l) chloride / N,N-dimethyl-formamide / Inert atmosphere; Cooling

2: tin(II) chloride dihdyrate / 11 h / 75 °C / Inert atmosphere

3: acetic acid; sodium nitrite / 15 - 20 °C / Inert atmosphere

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 2.5 h / 90 °C / Inert atmosphere

5: caesium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tin(II) chloride dihdyrate; N,N,N-trimethylhydrazinium iodide; potassium carbonate; caesium carbonate; acetic acid; copper(l) chloride; sodium nitrite; In N,N-dimethyl-formamide;

DOI:10.1021/jm2010173

Reference yield:

4-(3-bromo-5-chlorophenoxy)-5-chloro-1H-benzotriazole (1034474-44-6) → tert-butyl 3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (1034474-40-2)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 2.5 h / 90 °C / Inert atmosphere

2: caesium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In N,N-dimethyl-formamide;

DOI:10.1021/jm2010173

upstream raw materials:

3-chloro-5-[(5-chloro-1H-1,2,3-benzotriazol-4-yl)oxy]benzonitrile

3-bromomethylpyrazolo[3,4-b]pyridine-1-carboxylic acid tert-butyl ester

2-(3-bromo-5-chlorophenoxy)-1-chloro-3-nitrobenzene

3-(3-bromo-5-chlorophenoxy)-4-chloro-2-nitroaniline

Downstream raw materials:

3-chloro-5-{[5-chloro-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1H-1,2,3-benzotriazol-4-yl]oxy}benzonitrile

tert-butyl {2-[[(3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridin-1-yl)carbonyl](methyl)amino]ethyl}carbamate

tert-butyl {2-[[(3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridin-1-yl)carbonyl](methyl)amino]ethyl}methylcarbamate

2-[[(3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridin-1-yl)carbonyl](methyl)amino]ethanaminium chloride