methyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

Base Information

• Chemical Name: methyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate
• CAS No.: 1477524-10-9
• Molecular Formula: C₂₁H₂₄N₂O₃
• Molecular Weight: 352.433
• Mol file: 1477524-10-9.mol

Synonyms:methyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

Chemical Property of methyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

There total 8 articles about methyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate 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: 65.0%

6-bromopyridine-3-amine (13534-97-9) + methyl 2-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (1477524-09-6) → methyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (1477524-10-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; at 120 ℃; for 0.833333h; Microwave irradiation;

Reference yield:

(8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decan-8-yl)methanol (1477524-05-2) → methyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (1477524-10-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene-4-sulfonic acid / acetone; water / 1 h / 75 °C

2.1: sodium hydride / methanol / 0.5 h / 20 °C

2.2: 20 °C

3.1: sodium hydride / 1,4-dioxane / 0.67 h / 20 - 100 °C / Cooling with ice

4.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 °C / Inert atmosphere

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane / 0.83 h / 120 °C / Microwave irradiation

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; sodium hydride; sodium carbonate; toluene-4-sulfonic acid; In 1,4-dioxane; methanol; water; acetone; 2.1: |Wittig Olefination / 2.2: |Wittig Olefination / 4.1: |Suzuki Coupling;

Reference yield:

4-(4-bromophenyl)-4-(hydroxymethyl)cyclohexan-1-one (1477524-06-3) → methyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (1477524-10-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / methanol / 0.5 h / 20 °C

1.2: 20 °C

2.1: sodium hydride / 1,4-dioxane / 0.67 h / 20 - 100 °C / Cooling with ice

3.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 °C / Inert atmosphere

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane / 0.83 h / 120 °C / Microwave irradiation

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; sodium hydride; sodium carbonate; In 1,4-dioxane; methanol; 1.1: |Wittig Olefination / 1.2: |Wittig Olefination / 3.1: |Suzuki Coupling;

upstream raw materials:

methyl 8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decane-8-carboxylate

(8-(4-bromophenyl)-1,4-dioxaspiro[4.5]decan-8-yl)methanol

4-(4-bromophenyl)-4-(hydroxymethyl)cyclohexan-1-one

methyl 2-(4-(4-bromophenyl)-4-(hydroxymethyl)cyclohexylidene)acetate

Downstream raw materials:

2-(4-(4-(5-(2-ethyl-4-methyloxazole-5-carboxamido)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid

benzyl 2-(4-(4-(5-((5-(tert-butyl)oxazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

2-(4-(4-(5-((5-(tert-butyl)oxazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid

2-(4-(4-(5-(5-tert-butyl-1,3,4-oxadiazol-2-ylamino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetic acid