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

Base Information

• Chemical Name: 6-ethyl-1-methyl-5-[(phenylcarbonyl)amino]-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid
• CAS No.: 1269028-97-8
• Molecular Formula: C₂₀H₁₈F₃N₃O₄
• Molecular Weight: 421.376

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

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

Chemical Property:

Purity/Quality:

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

There total 18 articles about 6-ethyl-1-methyl-5-[(phenylcarbonyl)amino]-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid 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: 88.0%

ethyl 5-amino-6-ethyl-1-methyl-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[3,2-b]pyridine-2-carboxylate (1269028-95-6) + benzoyl chloride (98-88-4) → 6-ethyl-1-methyl-5-[(phenylcarbonyl)amino]-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid (1269028-97-8)

Guidance literature:

ethyl 5-amino-6-ethyl-1-methyl-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[3,2-b]pyridine-2-carboxylate; benzoyl chloride; With pyridine; In tetrahydrofuran; at 50 ℃; for 2h;

With water; sodium hydroxide; In ethanol; at 50 ℃; for 1h;

DOI:10.1016/j.bmc.2015.05.036

Reference yield:

5-Ethylpyridin-2-carbonsaeureethylester (13509-15-4) → 6-ethyl-1-methyl-5-[(phenylcarbonyl)amino]-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid (1269028-97-8)

Guidance literature:

Multi-step reaction with 16 steps

1.1: m-chloroperoxybenzoic acid / acetonitrile / 20 h / 20 °C

2.1: trifluoroacetic anhydride / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

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

4.1: silver carbonate / toluene / 2 h / 40 °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: tert-butyl alcohol / 18 h / 90 °C

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

8.2: 2 h / 0 °C

9.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 110 °C

10.1: sodium ethanolate / ethanol / 1 h / 20 °C

11.1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C

12.1: palladium 10% on activated carbon; hydrogen / ethanol; tetrahydrofuran / 1 h / 20 °C

13.1: pyridine / 16 h / 0 - 60 °C / Inert atmosphere

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

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

16.1: pyridine / tetrahydrofuran / 2 h / 50 °C

16.2: 1 h / 50 °C

With pyridine; hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-Bromosuccinimide; m-chloroperoxybenzoic acid; palladium 10% on activated carbon; water; hydrogen; sodium ethanolate; caesium carbonate; N-ethyl-N,N-diisopropylamine; silver carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trifluoroacetic anhydride; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1016/j.bmc.2015.05.036

Reference yield:

ethyl 5-ethylpyridine-2-carboxylate 1-oxide (1269028-76-3) → 6-ethyl-1-methyl-5-[(phenylcarbonyl)amino]-3-(2,2,2-trifluoroethoxy)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid (1269028-97-8)

Guidance literature:

Multi-step reaction with 15 steps

1.1: trifluoroacetic anhydride / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

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

3.1: silver carbonate / toluene / 2 h / 40 °C

4.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / toluene / 22 h / 100 °C / Inert atmosphere

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

6.1: tert-butyl alcohol / 18 h / 90 °C

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

7.2: 2 h / 0 °C

8.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 110 °C

9.1: sodium ethanolate / ethanol / 1 h / 20 °C

10.1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C

11.1: palladium 10% on activated carbon; hydrogen / ethanol; tetrahydrofuran / 1 h / 20 °C

12.1: pyridine / 16 h / 0 - 60 °C / Inert atmosphere

13.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / toluene / 22 h / 100 °C / Inert atmosphere

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

15.1: pyridine / tetrahydrofuran / 2 h / 50 °C

15.2: 1 h / 50 °C

With pyridine; hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-Bromosuccinimide; palladium 10% on activated carbon; water; hydrogen; sodium ethanolate; caesium carbonate; N-ethyl-N,N-diisopropylamine; silver carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; trifluoroacetic anhydride; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1016/j.bmc.2015.05.036

upstream raw materials:

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

benzoyl chloride

5-Ethylpyridin-2-carbonsaeureethylester

ethyl 5-ethylpyridine-2-carboxylate 1-oxide

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