2-[6-(3-fluoro-4-methoxybenzyl)-1,2,3,7-tetrahydro-4H-indolo[2,3-c][1,8]naphthyridin-4-yl]acetamide

Base Information

• Chemical Name: 2-[6-(3-fluoro-4-methoxybenzyl)-1,2,3,7-tetrahydro-4H-indolo[2,3-c][1,8]naphthyridin-4-yl]acetamide
• CAS No.: 1265773-90-7
• Molecular Formula: C₂₄H₂₃FN₄O₂
• Molecular Weight: 418.471
• Mol file: 1265773-90-7.mol

Synonyms:2-[6-(3-fluoro-4-methoxybenzyl)-1,2,3,7-tetrahydro-4H-indolo[2,3-c][1,8]naphthyridin-4-yl]acetamide

Chemical Property of 2-[6-(3-fluoro-4-methoxybenzyl)-1,2,3,7-tetrahydro-4H-indolo[2,3-c][1,8]naphthyridin-4-yl]acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[6-(3-fluoro-4-methoxybenzyl)-1,2,3,7-tetrahydro-4H-indolo[2,3-c][1,8]naphthyridin-4-yl]acetamide

There total 13 articles about 2-[6-(3-fluoro-4-methoxybenzyl)-1,2,3,7-tetrahydro-4H-indolo[2,3-c][1,8]naphthyridin-4-yl]acetamide 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:

bromo-acetic acid amide (683-57-8) + 6-(3-fluoro-4-methoxybenzyl)-2,3,4,7-tetrahydro-1H-indolo[2,3-c][1,8]naphthyridine (1265773-80-5) → 2-[6-(3-fluoro-4-methoxybenzyl)-1,2,3,7-tetrahydro-4H-indolo[2,3-c][1,8]naphthyridin-4-yl]acetamide (1265773-90-7)

Guidance literature:

With triethylamine; potassium iodide; In N,N-dimethyl-formamide; at 130 - 150 ℃; for 2h; sealed tube; microwave irradiation;

Reference yield:

ethyl 3-indoleacetate (778-82-5) → 2-[6-(3-fluoro-4-methoxybenzyl)-1,2,3,7-tetrahydro-4H-indolo[2,3-c][1,8]naphthyridin-4-yl]acetamide (1265773-90-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: dmap; triethylamine / dichloromethane / 18 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

2.2: 1.55 h / 20 - 30 °C

3.1: zinc(II) chloride / 1,1-dichloroethane; diethyl ether / 0.08 h / 0 °C / Inert atmosphere

3.2: 1.67 h / 0 - 20 °C

3.3: 0.5 h / 150 °C / sealed tube; microwave irradiation

4.1: pyridine / dichloromethane / 1.5 h / 0 °C

5.1: dmap; triethylamine / dichloromethane / 18 h / 20 °C

6.1: caesium carbonate / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere

7.1: cyclohexa-1,4-diene / palladium 10% on activated carbon / butan-1-ol / 18 h / Inert atmosphere; Reflux

8.1: thionyl chloride / dichloromethane / Reflux

9.1: potassium iodide; triethylamine / N,N-dimethyl-formamide / 0.5 h / 100 °C / sealed tube; microwave irradiation

10.1: potassium iodide; triethylamine / N,N-dimethyl-formamide / 2 h / 130 - 150 °C / sealed tube; microwave irradiation

With pyridine; dmap; thionyl chloride; cyclohexa-1,4-diene; sodium hydride; caesium carbonate; triethylamine; potassium iodide; zinc(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium 10% on activated carbon; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; diethyl ether; 1,1-dichloroethane; dichloromethane; N,N-dimethyl-formamide; mineral oil; butan-1-ol;

Reference yield:

tert-butyl 3-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate (786647-50-5) → 2-[6-(3-fluoro-4-methoxybenzyl)-1,2,3,7-tetrahydro-4H-indolo[2,3-c][1,8]naphthyridin-4-yl]acetamide (1265773-90-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

1.2: 1.55 h / 20 - 30 °C

2.1: zinc(II) chloride / 1,1-dichloroethane; diethyl ether / 0.08 h / 0 °C / Inert atmosphere

2.2: 1.67 h / 0 - 20 °C

2.3: 0.5 h / 150 °C / sealed tube; microwave irradiation

3.1: pyridine / dichloromethane / 1.5 h / 0 °C

4.1: dmap; triethylamine / dichloromethane / 18 h / 20 °C

5.1: caesium carbonate / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere

6.1: cyclohexa-1,4-diene / palladium 10% on activated carbon / butan-1-ol / 18 h / Inert atmosphere; Reflux

7.1: thionyl chloride / dichloromethane / Reflux

8.1: potassium iodide; triethylamine / N,N-dimethyl-formamide / 0.5 h / 100 °C / sealed tube; microwave irradiation

9.1: potassium iodide; triethylamine / N,N-dimethyl-formamide / 2 h / 130 - 150 °C / sealed tube; microwave irradiation

With pyridine; dmap; thionyl chloride; cyclohexa-1,4-diene; sodium hydride; caesium carbonate; triethylamine; potassium iodide; zinc(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; palladium 10% on activated carbon; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; diethyl ether; 1,1-dichloroethane; dichloromethane; N,N-dimethyl-formamide; mineral oil; butan-1-ol;

upstream raw materials:

bromo-acetic acid amide

6-(3-fluoro-4-methoxybenzyl)-2,3,4,7-tetrahydro-1H-indolo[2,3-c][1,8]naphthyridine

ethyl 3-indoleacetate

tert-butyl 3-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate