ethyl 6-ethyl-1-methyl-5-[(phenylcarbonyl)amino]-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

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Chemical Name:ethyl 6-ethyl-1-methyl-5-[(phenylcarbonyl)amino]-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate
CAS No.:1269024-90-9
Molecular Formula:C₂₂H₂₂F₃N₃O₄
Molecular Weight:449.43
Hs Code.:

Synonyms:ethyl 6-ethyl-1-methyl-5-[(phenylcarbonyl)amino]-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

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Chemical Property of ethyl 6-ethyl-1-methyl-5-[(phenylcarbonyl)amino]-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

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Technology Process of ethyl 6-ethyl-1-methyl-5-[(phenylcarbonyl)amino]-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

There total 11 articles about ethyl 6-ethyl-1-methyl-5-[(phenylcarbonyl)amino]-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[2,3-b]pyridine-2-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: 14.0%

: 1269024-75-0
ethyl 5-amino-6-ethyl-1-methyl-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

: 98-88-4
benzoyl chloride

: 1269024-90-9
ethyl 6-ethyl-1-methyl-5-[(phenylcarbonyl)amino]-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Guidance literature:: With pyridine; In tetrahydrofuran; at 0 - 20 ℃; for 1.5h;
DOI:10.1016/j.bmc.2015.05.036

Reference yield:

: 1186188-51-1
ethyl 4-chloro-6-ethyl-2-oxo-1,2-dihydropyridine-3-carboxylate

: 1269024-90-9
ethyl 6-ethyl-1-methyl-5-[(phenylcarbonyl)amino]-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: triethylamine; palladium 10% on activated carbon; hydrogen / ethanol; tetrahydrofuran / 5 h / 20 °C

2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 0 - 20 °C

3.1: trichlorophosphate / 12 h / Reflux

4.1: triethylamine / 39 h / Reflux

4.2: 1 h / 20 °C

5.1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C

6.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 22 h / 100 °C / Inert atmosphere

7.1: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C

8.1: pyridine / tetrahydrofuran / 1.5 h / 0 - 20 °C

With pyridine; hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-Bromosuccinimide; palladium 10% on activated carbon; water; hydrogen; caesium carbonate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trichlorophosphate; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmc.2015.05.036

Reference yield:

: 1269024-68-1
ethyl 6-ethyl-2-oxo-1,2-dihydropyridine-3-carboxylate

: 1269024-90-9
ethyl 6-ethyl-1-methyl-5-[(phenylcarbonyl)amino]-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 0 - 20 °C

2.1: trichlorophosphate / 12 h / Reflux

3.1: triethylamine / 39 h / Reflux

3.2: 1 h / 20 °C

4.1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C

5.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 22 h / 100 °C / Inert atmosphere

6.1: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C

7.1: pyridine / tetrahydrofuran / 1.5 h / 0 - 20 °C

With pyridine; hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-Bromosuccinimide; water; caesium carbonate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trichlorophosphate; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmc.2015.05.036