3-({1-[(6-amino-1H-pyrazolo[3,4-b]pyridin-3-yl)methyl]-5-chloro-1H-indazol-4-yl}oxy)-5-chlorobenzonitrile

Base Information

• Chemical Name: 3-({1-[(6-amino-1H-pyrazolo[3,4-b]pyridin-3-yl)methyl]-5-chloro-1H-indazol-4-yl}oxy)-5-chlorobenzonitrile
• CAS No.: 1034474-35-5
• Molecular Formula: C₂₁H₁₃Cl₂N₇O
• Molecular Weight: 450.287
• Mol file: 1034474-35-5.mol

Synonyms:3-({1-[(6-amino-1H-pyrazolo[3,4-b]pyridin-3-yl)methyl]-5-chloro-1H-indazol-4-yl}oxy)-5-chlorobenzonitrile

Chemical Property of 3-({1-[(6-amino-1H-pyrazolo[3,4-b]pyridin-3-yl)methyl]-5-chloro-1H-indazol-4-yl}oxy)-5-chlorobenzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-({1-[(6-amino-1H-pyrazolo[3,4-b]pyridin-3-yl)methyl]-5-chloro-1H-indazol-4-yl}oxy)-5-chlorobenzonitrile

There total 12 articles about 3-({1-[(6-amino-1H-pyrazolo[3,4-b]pyridin-3-yl)methyl]-5-chloro-1H-indazol-4-yl}oxy)-5-chlorobenzonitrile 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%

3-chloro-5-{[5-chloro-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-1H-indazol-4-yl]oxy}benzonitrile (1034474-34-4) → 3-({1-[(6-amino-1H-pyrazolo[3,4-b]pyridin-3-yl)methyl]-5-chloro-1H-indazol-4-yl}oxy)-5-chlorobenzonitrile (1034474-35-5)

Guidance literature:

With trifluoroacetic acid; at 75 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm2010173

Reference yield:

3-bromo-5-chlorophenyl 2-chloro-5-fluorophenyl ether (1034474-29-7) → 3-({1-[(6-amino-1H-pyrazolo[3,4-b]pyridin-3-yl)methyl]-5-chloro-1H-indazol-4-yl}oxy)-5-chlorobenzonitrile (1034474-35-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; hexane; ethylbenzene / 0.5 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: hydrazine hydrate / ethanol / 96 h / 95 °C / Inert atmosphere

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

4.1: lithium tert-butoxide / N,N-dimethyl-formamide / Inert atmosphere

4.2: 25 °C / Cooling with ice; Inert atmosphere

5.1: trifluoroacetic acid / 2 h / 75 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrazine hydrate; trifluoroacetic acid; lithium tert-butoxide; lithium diisopropyl amide; In tetrahydrofuran; ethanol; hexane; ethylbenzene; N,N-dimethyl-formamide;

DOI:10.1021/jm2010173

Reference yield:

2-(3-bromo-5-chlorophenoxy)-3-chloro-6-fluorobenzaldehyde (1034474-30-0) → 3-({1-[(6-amino-1H-pyrazolo[3,4-b]pyridin-3-yl)methyl]-5-chloro-1H-indazol-4-yl}oxy)-5-chlorobenzonitrile (1034474-35-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: hydrazine hydrate / ethanol / 96 h / 95 °C / Inert atmosphere

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

3.1: lithium tert-butoxide / N,N-dimethyl-formamide / Inert atmosphere

3.2: 25 °C / Cooling with ice; Inert atmosphere

4.1: trifluoroacetic acid / 2 h / 75 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrazine hydrate; trifluoroacetic acid; lithium tert-butoxide; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm2010173

upstream raw materials:

3-chloro-5-{[5-chloro-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-1H-indazol-4-yl]oxy}benzonitrile

tert-butyl 1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridine-3-carboxylate

3-bromo-5-chlorophenyl 2-chloro-5-fluorophenyl ether

2-(3-bromo-5-chlorophenoxy)-3-chloro-6-fluorobenzaldehyde

Downstream raw materials:

3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-indazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridin-6-aminium chloride