4-[6-(3-pyrazol-1-yl-phenyl)-pyridin-3-yl]-1-aza-bicyclo[2.2.1]heptane

Base Information

• Chemical Name: 4-[6-(3-pyrazol-1-yl-phenyl)-pyridin-3-yl]-1-aza-bicyclo[2.2.1]heptane
• CAS No.: 1046834-15-4
• Molecular Formula: C₂₀H₂₀N₄
• Molecular Weight: 316.406
• Mol file: 1046834-15-4.mol

Synonyms:4-[6-(3-pyrazol-1-yl-phenyl)-pyridin-3-yl]-1-aza-bicyclo[2.2.1]heptane

Chemical Property of 4-[6-(3-pyrazol-1-yl-phenyl)-pyridin-3-yl]-1-aza-bicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[6-(3-pyrazol-1-yl-phenyl)-pyridin-3-yl]-1-aza-bicyclo[2.2.1]heptane

There total 16 articles about 4-[6-(3-pyrazol-1-yl-phenyl)-pyridin-3-yl]-1-aza-bicyclo[2.2.1]heptane 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: 61.0%

4-(6-bromopyridin-3-yl)-1-azabicyclo[2.2.1]heptane (1238104-52-3) + 1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1H-pyrazole (852227-94-2) → 4-[6-(3-pyrazol-1-yl-phenyl)-pyridin-3-yl]-1-aza-bicyclo[2.2.1]heptane (1046834-15-4)

Guidance literature:

With trans-bis(triphenylphosphine)palladium dichloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 110 ℃; for 0.166667h; Microwave irradiation;

DOI:10.1021/jo201501f

Reference yield: 48.0%

4-(6-chloro-pyridin-3-yl)-1-aza-bicyclo[2.2.1]heptane (1046834-25-6) + 1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1H-pyrazole (852227-94-2) → 4-[6-(3-pyrazol-1-yl-phenyl)-pyridin-3-yl]-1-aza-bicyclo[2.2.1]heptane (1046834-15-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,2-dimethoxyethane; water; Inert atmosphere; Reflux;

DOI:10.1021/ol102170q

Reference yield:

3-cyano-3-(pyridin-3-yl)-pentanedioic acid diethyl ester (167263-47-0) → 4-[6-(3-pyrazol-1-yl-phenyl)-pyridin-3-yl]-1-aza-bicyclo[2.2.1]heptane (1046834-15-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: hydrogen / ethanol; water / 6 h / 70 °C / 5250.53 Torr

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 50 °C / Inert atmosphere

3.1: water; hydrogen bromide / 150 °C

4.1: potassium carbonate / chloroform; water / 50 °C

5.1: n-butyllithium; 2-(N,N-dimethylamino)ethanol / hexane; n-heptane / 1 h / -20 °C / Inert atmosphere

5.2: -78 - 20 °C / Inert atmosphere

6.1: trans-bis(triphenylphosphine)palladium dichloride; potassium carbonate / 1,2-dimethoxyethane; water / 3 h / Reflux

With lithium aluminium tetrahydride; n-butyllithium; 2-(N,N-dimethylamino)ethanol; trans-bis(triphenylphosphine)palladium dichloride; water; hydrogen bromide; hydrogen; potassium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; n-heptane; chloroform; water; 6.1: Suzuki-Miyaura coupling;

DOI:10.1021/jo201501f

upstream raw materials:

4-(6-chloro-pyridin-3-yl)-1-aza-bicyclo[2.2.1]heptane

1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1H-pyrazole

3-pyridinylacetonitrile

5-[3-(2-bromo-ethyl)-pyrrolidin-3-yl]-pyridin-2-ol hydrobromide