tert-butyl 3-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 3-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate
• CAS No.: 877399-36-5
• Molecular Formula: C₂₄H₂₆Cl₂FN₅O₃
• Molecular Weight: 522.407
• Mol file: 877399-36-5.mol

Synonyms:tert-butyl 3-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate

Chemical Property of tert-butyl 3-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 3-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate

There total 9 articles about tert-butyl 3-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)azetidine-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: 92.0%

5-iodo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine (756520-48-6) + tert-butyl 3-(4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)-azetidine-1-carboxylate (877399-35-4) → tert-butyl 3-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate (877399-36-5)

Guidance literature:

5-iodo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine; tert-butyl 3-(4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)-azetidine-1-carboxylate; In ethylene glycol dimethylether; for 0.25h;

bis-triphenylphosphine-palladium(II) chloride; In ethylene glycol dimethylether; for 0.25h;

With sodium carbonate; In ethylene glycol dimethylether; water; at 85 ℃;

Reference yield: 92.0%

(±)-5-bromo-3-(1-(2,6-dichloro-3-fluoropheny)ethoxy)pyridin-2-amine (756503-69-2,1448326-33-7,877399-00-3) + tert-butyl 3-(4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)-azetidine-1-carboxylate (877399-35-4) → tert-butyl 3-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate (877399-36-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,2-dimethoxyethane; water; at 85 ℃; Inert atmosphere;

DOI:10.1021/jm2007613

Reference yield:

tert-butyl 3-hydroxyazetidine-1-carboxylate (141699-55-0) → tert-butyl 3-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate (877399-36-5)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2: caesium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere

3: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / 1,2-dimethoxyethane; water / 85 °C / Inert atmosphere

With dmap; bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; caesium carbonate; triethylamine; In 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; 3: Suzuki coupling;

DOI:10.1021/jm2007613

upstream raw materials:

5-iodo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine

tert-butyl 3-(4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)-azetidine-1-carboxylate

1-(2,6-dichloro-3-fluorophenyl)ethanol

tert-butyl 3-(4-bromo-1H-pyrazol-1-yl)azetidine-1-carboxylate

Downstream raw materials:

5-(1-(azetidin-3-yl)-1H-pyrazol-4-yl)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine