ethyl 5-{6-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyridazin-3-yl}nicotinate

Base Information

• Chemical Name: ethyl 5-{6-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyridazin-3-yl}nicotinate
• CAS No.: 1020658-16-5
• Molecular Formula: C₂₃H₂₂BrFN₄O₃
• Molecular Weight: 501.355
• Mol file: 1020658-16-5.mol

Synonyms:ethyl 5-{6-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyridazin-3-yl}nicotinate

Chemical Property of ethyl 5-{6-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyridazin-3-yl}nicotinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 5-{6-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyridazin-3-yl}nicotinate

There total 3 articles about ethyl 5-{6-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyridazin-3-yl}nicotinate 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%

ethyl 5-[6-(4-hydroxypiperidin-1-yl)pyridazin-3-yl]nicotinate (1020658-45-0) + 2-bromo-5-fluorophenol (147460-41-1) → ethyl 5-{6-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyridazin-3-yl}nicotinate (1020658-16-5)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 16h; Sonication;

DOI:10.1016/j.bmcl.2011.10.040

Reference yield:

4-HYDROXYPIPERIDINE (5382-16-1) → ethyl 5-{6-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyridazin-3-yl}nicotinate (1020658-16-5)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride / water / 24 h / 80 °C

2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate; tricyclohexylphosphine / 1,4-dioxane; water / 3 h / 100 °C

3: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 16 h / Sonication

With hydrogenchloride; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenylphosphine; diethylazodicarboxylate; tricyclohexylphosphine; In tetrahydrofuran; 1,4-dioxane; water; 2: Suzuki coupling / 3: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2011.10.040

Reference yield:

1-(6-chloro-pyridazin-3-yl)-piperidin-4-ol (89937-26-8) → ethyl 5-{6-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyridazin-3-yl}nicotinate (1020658-16-5)

Guidance literature:

Multi-step reaction with 2 steps

1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium phosphate; tricyclohexylphosphine / 1,4-dioxane; water / 3 h / 100 °C

2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 16 h / Sonication

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenylphosphine; diethylazodicarboxylate; tricyclohexylphosphine; In tetrahydrofuran; 1,4-dioxane; water; 1: Suzuki coupling / 2: Mitsunobu reaction;

DOI:10.1016/j.bmcl.2011.10.040

upstream raw materials:

ethyl 5-[6-(4-hydroxypiperidin-1-yl)pyridazin-3-yl]nicotinate

2-bromo-5-fluorophenol

4-HYDROXYPIPERIDINE

1-(6-chloro-pyridazin-3-yl)-piperidin-4-ol

Downstream raw materials:

5-{6-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]pyridazin-3-yl}-nicotinic acid