4-(3-amino-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide

Base Information

• Chemical Name: 4-(3-amino-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide
• CAS No.: 1352835-83-6
• Molecular Formula: C₂₁H₁₉FN₄O₃
• Molecular Weight: 394.405
• Mol file: 1352835-83-6.mol

Synonyms:4-(3-amino-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide

Chemical Property of 4-(3-amino-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(3-amino-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide

There total 11 articles about 4-(3-amino-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide 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%

benzyl 3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-fluorophenylcarbamate (1352835-82-5) → 4-(3-amino-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide (1352835-83-6)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In tetrahydrofuran; methanol; for 2h;

Reference yield:

6-hydroxy-1H-indole (2380-86-1) → 4-(3-amino-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide (1352835-83-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 75 °C

2.1: 125 °C

3.1: zinc; ammonium chloride / tetrahydrofuran; methanol / 3 h / Inert atmosphere

3.2: pH ~ 11

4.1: hydrogenchloride / toluene; 1,4-dioxane / 16 h / 20 °C

4.2: pH 10

4.3: 3.5 h / 125 °C

5.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 1.5 h

5.2: pH 4 - 5

6.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; 4-methyl-morpholine; ammonium chloride / N,N-dimethyl-formamide / 2 h / Inert atmosphere

7.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran; methanol / 2 h

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide monohydrate; water; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; ammonium chloride; caesium carbonate; N-ethyl-N,N-diisopropylamine; zinc; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; toluene;

Reference yield:

3-amino-2-fluorobenzonitrile (873697-68-8) → 4-(3-amino-2-fluorophenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide (1352835-83-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: potassium carbonate / tetrahydrofuran / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; tetrahydrofuran / 5.75 h / -78 - 20 °C / Inert atmosphere

2.2: 1.33 h / Cooling with ice

3.1: acetic acid / 2 h / 90 °C / Inert atmosphere

4.1: 125 °C

5.1: zinc; ammonium chloride / tetrahydrofuran; methanol / 3 h / Inert atmosphere

5.2: pH ~ 11

6.1: hydrogenchloride / toluene; 1,4-dioxane / 16 h / 20 °C

6.2: pH 10

6.3: 3.5 h / 125 °C

7.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 1.5 h

7.2: pH 4 - 5

8.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; 4-methyl-morpholine; ammonium chloride / N,N-dimethyl-formamide / 2 h / Inert atmosphere

9.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran; methanol / 2 h

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide monohydrate; water; hydrogen; diisobutylaluminium hydride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; ammonium chloride; acetic acid; N-ethyl-N,N-diisopropylamine; zinc; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

6-hydroxy-1H-indole

3-amino-2-fluorobenzonitrile

benzyl 3-cyano-2-fluorophenylcarbamate

benzyl 2-fluoro-3-formylphenylcarbamate

Downstream raw materials:

2-((3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-fluorophenylamino)methyl)-5-methylbenzoic acid