3-chloro-5-{[5-chloro-2-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-2H-indazol-4-yl]oxy}benzonitrile

Base Information

• Chemical Name: 3-chloro-5-{[5-chloro-2-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-2H-indazol-4-yl]oxy}benzonitrile
• CAS No.: 1345337-17-8
• Molecular Formula: C₃₇H₂₉Cl₂N₇O₃
• Molecular Weight: 690.588
• Mol file: 1345337-17-8.mol

Synonyms:3-chloro-5-{[5-chloro-2-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-2H-indazol-4-yl]oxy}benzonitrile

Chemical Property of 3-chloro-5-{[5-chloro-2-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-2H-indazol-4-yl]oxy}benzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-chloro-5-{[5-chloro-2-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-2H-indazol-4-yl]oxy}benzonitrile

There total 11 articles about 3-chloro-5-{[5-chloro-2-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-2H-indazol-4-yl]oxy}benzonitrile 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: 56.2%

3-chloro-5-[(5-chloro-1H-indazol-4-yl)oxy]benzonitrile (1034474-32-2) + 3-(chloromethyl)-N,1-bis(methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-6-amine (1034474-25-3) → 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-chloro-5-{[5-chloro-2-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-2H-indazol-4-yl]oxy}benzonitrile (1345337-17-8)

Guidance literature:

3-chloro-5-[(5-chloro-1H-indazol-4-yl)oxy]benzonitrile; With lithium tert-butoxide; In N,N-dimethyl-formamide; Inert atmosphere;

3-(chloromethyl)-N,1-bis(methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-6-amine; In N,N-dimethyl-formamide; at 25 ℃; Cooling with ice; Inert atmosphere;

DOI:10.1021/jm2010173

Reference yield:

tert-butyl 1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (1034474-27-5) → 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-chloro-5-{[5-chloro-2-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-2H-indazol-4-yl]oxy}benzonitrile (1345337-17-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 25 °C / Inert atmosphere

2.1: thionyl chloride / chloroform / 20 °C / Cooling with ice; Inert atmosphere

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

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

With lithium aluminium tetrahydride; thionyl chloride; lithium tert-butoxide; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jm2010173

Reference yield:

3-bromo-5-chlorophenyl 2-chloro-5-fluorophenyl ether (1034474-29-7) → 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-chloro-5-{[5-chloro-2-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-2H-indazol-4-yl]oxy}benzonitrile (1345337-17-8)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/jm2010173

upstream raw materials:

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

4-(3-bromo-5-chlorophenoxy)-5-chloro-1H-indazole