ethyl 5-((2R,4S)-2-(3-cyano-5-fluorophenyl)-4-fluoropyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylate

Base Information

• Chemical Name: ethyl 5-((2R,4S)-2-(3-cyano-5-fluorophenyl)-4-fluoropyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylate
• CAS No.: 1394838-08-4
• Molecular Formula: C₂₁H₁₈F₂N₄O₂
• Molecular Weight: 396.396
• Mol file: 1394838-08-4.mol

Synonyms:ethyl 5-((2R,4S)-2-(3-cyano-5-fluorophenyl)-4-fluoropyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylate

Chemical Property of ethyl 5-((2R,4S)-2-(3-cyano-5-fluorophenyl)-4-fluoropyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 5-((2R,4S)-2-(3-cyano-5-fluorophenyl)-4-fluoropyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylate

There total 12 articles about ethyl 5-((2R,4S)-2-(3-cyano-5-fluorophenyl)-4-fluoropyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-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:

ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate (885276-93-7) + 3-fluoro-5-((2R,4S)-4-fluoropyrrolidin-2-yl)benzonitrile (1364890-34-5) → ethyl 5-((2R,4S)-2-(3-cyano-5-fluorophenyl)-4-fluoropyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylate (1394838-08-4)

Guidance literature:

With caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 140 ℃; for 0.416667h; Inert atmosphere; Microwave;

Reference yield:

(2R,4S)-tert-butyl 2-(3-cyano-5-fluorophenyl)-4-fluoropyrrolidine-1-carboxylate (1364890-33-4) → ethyl 5-((2R,4S)-2-(3-cyano-5-fluorophenyl)-4-fluoropyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylate (1394838-08-4)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

2: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 0.42 h / 140 °C / Inert atmosphere; Microwave

With caesium carbonate; trifluoroacetic acid; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; dichloromethane;

Reference yield:

(3R)-4-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)-1-(3-cyano-5-fluorophenyl)butyl methanesulfonate → ethyl 5-((2R,4S)-2-(3-cyano-5-fluorophenyl)-4-fluoropyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylate (1394838-08-4)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 12 h / 20 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

3: diethylamino-sulfur trifluoride / dichloromethane / 2 h / -78 °C

4: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

5: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 0.42 h / 140 °C / Inert atmosphere; Microwave

With diethylamino-sulfur trifluoride; tetrabutyl ammonium fluoride; sodium hydride; caesium carbonate; trifluoroacetic acid; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate

3-fluoro-5-((2R,4S)-4-fluoropyrrolidin-2-yl)benzonitrile

3-fluoro-5-formylbenzonitrile

tert-butyl ((2R)-2-((tert-butyldimethylsilyl)oxy)-4-(3-cyano-5-fluorophenyl)-4-hydroxybutyl)carbamate

Refernces