ethyl 2-(8-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-5-carboxamido)acetate

Base Information

• Chemical Name: ethyl 2-(8-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-5-carboxamido)acetate
• CAS No.: 1578241-35-6
• Molecular Formula: C₂₃H₁₈Cl₂F₃N₃O₄
• Molecular Weight: 528.315

Synonyms:ethyl 2-(8-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-5-carboxamido)acetate

Chemical Property of ethyl 2-(8-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-5-carboxamido)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of ethyl 2-(8-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-5-carboxamido)acetate

There total 14 articles about ethyl 2-(8-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-5-carboxamido)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: 84.0%

8-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazol-3-yl)indolizine-5-carboxylic acid (1437053-90-1) + GlyOEt*HCl (459-73-4) → ethyl 2-(8-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-5-carboxamido)acetate (1578241-35-6)

Guidance literature:

8-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazol-3-yl)indolizine-5-carboxylic acid; With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h;

GlyOEt*HCl; at 20 ℃; for 16h;

DOI:10.1016/j.tetlet.2014.02.003

Reference yield:

5-methyl-6,7-dihydro-5H-indolizin-8-one (864426-31-3) → ethyl 2-(8-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-5-carboxamido)acetate (1578241-35-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: potassium permanganate; water / tert-butyl alcohol / 16 h / 70 °C

2.1: thionyl chloride / 5 h / 0 °C / Reflux

3.1: phenyltrimethylammonium tribromide / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 3 h / 20 °C

5.1: palladium on activated charcoal; hydrogen; potassium carbonate / ethyl acetate / 4 h / 20 °C

6.1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

7.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium bromide / 1,4-dioxane / 16 h / Reflux; Inert atmosphere

8.1: hydrogenchloride / water / 2 h / 20 °C

9.1: triethylamine / toluene / 24 h / 60 °C

10.1: acetic anhydride; triethylamine / 3 h / 20 °C

11.1: hydroxylamine hydrochloride; sodium hydroxide / tetrahydrofuran; water / 5 °C

12.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.25 h / 20 °C

12.2: 16 h / 20 °C

With hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium permanganate; thionyl chloride; palladium on activated charcoal; hydroxylamine hydrochloride; water; hydrogen; acetic anhydride; phenyltrimethylammonium tribromide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium bromide; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1016/j.tetlet.2014.02.003

Reference yield:

ethyl 8-oxo-5,6,7,8-tetrahydroindolizine-5-carboxylate (259683-86-8) → ethyl 2-(8-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-5-carboxamido)acetate (1578241-35-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: phenyltrimethylammonium tribromide / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 3 h / 20 °C

3.1: palladium on activated charcoal; hydrogen; potassium carbonate / ethyl acetate / 4 h / 20 °C

4.1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium bromide / 1,4-dioxane / 16 h / Reflux; Inert atmosphere

6.1: hydrogenchloride / water / 2 h / 20 °C

7.1: triethylamine / toluene / 24 h / 60 °C

8.1: acetic anhydride; triethylamine / 3 h / 20 °C

9.1: hydroxylamine hydrochloride; sodium hydroxide / tetrahydrofuran; water / 5 °C

10.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.25 h / 20 °C

10.2: 16 h / 20 °C

With hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium on activated charcoal; hydroxylamine hydrochloride; hydrogen; acetic anhydride; phenyltrimethylammonium tribromide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium bromide; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tetlet.2014.02.003

upstream raw materials:

5-methyl-6,7-dihydro-5H-indolizin-8-one

ethyl 8-oxo-5,6,7,8-tetrahydroindolizine-5-carboxylate

8-oxo-6,7-dihydro-5H-indolizine-5-carboxylic acid

ethyl 5,7-dibromo-8-oxo-5,6,7,8-tetrahydroindolizine-5-carboxylate

Downstream raw materials:

8-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)indolizine-5-carboxamide

C₂₁H₁₄Cl₂F₃N₃O₄

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