C₂₀H₁₇F₃N₄O₂

Base Information

• Chemical Name: C₂₀H₁₇F₃N₄O₂
• CAS No.: 1620328-11-1
• Molecular Formula: C₂₀H₁₇F₃N₄O₂
• Molecular Weight: 402.376
• Mol file: 1620328-11-1.mol

Synonyms:

Chemical Property of C₂₀H₁₇F₃N₄O₂

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₂₀H₁₇F₃N₄O₂

There total 15 articles about C₂₀H₁₇F₃N₄O₂ 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:

4-iodo-3-(trifluoromethyl)-1-tritylpyrazolo[5,4-b]pyridine (1160502-31-7) → C20H17F3N4O2 (1620328-11-1) + C20H17F3N4O2 (1620328-15-5)

Guidance literature:

Multi-step reaction with 4 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 14 h / 105 °C

2: potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate / tetrahydrofuran; water / 2.5 h / 20 °C

3: N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid; trifluoroacetic acid / dichloromethane / 2 h / 0 °C

4: Resolution of racemate

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid; potassium acetate; trifluoroacetic acid; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1: |Suzuki Coupling / 2: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2014.05.082

Reference yield:

1,3-dibromo-5-fluorobenzene (1435-51-4) → C20H17F3N4O2 (1620328-11-1) + C20H17F3N4O2 (1620328-15-5)

Guidance literature:

Multi-step reaction with 9 steps

1: sodium hydride / 1-methyl-pyrrolidin-2-one / 24 h / 120 °C

2: lithium chloride / dimethyl sulfoxide; water / 3 h / 165 °C

3: tetrabutylammomium bromide; sodium hydroxide / toluene; water / 16 h / 20 °C

4: copper(l) cyanide; TurboGrignard / tetrahydrofuran / 1 h / 0 - 20 °C

5: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 16 h / 20 °C

6: toluene-4-sulfonic acid / water; acetone / 16 h / 20 °C

7: potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate / tetrahydrofuran; water / 2.5 h / 20 °C

8: N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid; trifluoroacetic acid / dichloromethane / 2 h / 0 °C

9: Resolution of racemate

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; osmium(VIII) oxide; TurboGrignard; N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid; tetrabutylammomium bromide; copper(l) cyanide; sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; trifluoroacetic acid; lithium chloride; sodium hydroxide; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; dichloromethane; water; dimethyl sulfoxide; acetone; toluene; 2: |Krapcho Dealkoxycarbonylation / 7: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2014.05.082

Reference yield:

[(fluoro-2-iodo-4)pyrid-3-yl]-carboxaldehyde (153034-82-3) → C20H17F3N4O2 (1620328-11-1) + C20H17F3N4O2 (1620328-15-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / -10 - 0 °C

2.1: manganese(IV) oxide / toluene / 3 h / Reflux

3.1: hydrazine hydrate / 1,4-dioxane / 0.25 h / 50 °C

4.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C

4.2: 2 h / 20 °C

5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / N,N-dimethyl-formamide / 14 h / 105 °C

6.1: potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate / tetrahydrofuran; water / 2.5 h / 20 °C

7.1: N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid; trifluoroacetic acid / dichloromethane / 2 h / 0 °C

8.1: Resolution of racemate

With manganese(IV) oxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid; tetrabutyl ammonium fluoride; potassium acetate; sodium hydride; hydrazine hydrate; trifluoroacetic acid; tri tert-butylphosphoniumtetrafluoroborate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 5.1: |Suzuki Coupling / 6.1: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2014.05.082

upstream raw materials:

4-iodo-3-(trifluoromethyl)-1-tritylpyrazolo[5,4-b]pyridine

C₃₂H₂₉BF₃N₃O₂

1,3-dibromo-5-fluorobenzene

[(fluoro-2-iodo-4)pyrid-3-yl]-carboxaldehyde

Refernces