9-(1-benzyl-3,6-dihydro-2H-pyridin-5-yl)-3H-pyrrolo[3,2-f][1,7]naphthyridine

Base Information

• Chemical Name: 9-(1-benzyl-3,6-dihydro-2H-pyridin-5-yl)-3H-pyrrolo[3,2-f][1,7]naphthyridine
• CAS No.: 1401447-95-7
• Molecular Formula: C₂₂H₂₀N₄
• Molecular Weight: 340.428
• Mol file: 1401447-95-7.mol

Synonyms:9-(1-benzyl-3,6-dihydro-2H-pyridin-5-yl)-3H-pyrrolo[3,2-f][1,7]naphthyridine

Chemical Property of 9-(1-benzyl-3,6-dihydro-2H-pyridin-5-yl)-3H-pyrrolo[3,2-f][1,7]naphthyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-(1-benzyl-3,6-dihydro-2H-pyridin-5-yl)-3H-pyrrolo[3,2-f][1,7]naphthyridine

There total 18 articles about 9-(1-benzyl-3,6-dihydro-2H-pyridin-5-yl)-3H-pyrrolo[3,2-f][1,7]naphthyridine 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:

4-chloro-7-azaindole (55052-28-3) → 9-(1-benzyl-3,6-dihydro-2H-pyridin-5-yl)-3H-pyrrolo[3,2-f][1,7]naphthyridine (1401447-95-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dmap; triethylamine / dichloromethane / 12 h / 20 °C

2.1: trifluoroacetic anhydride; tetramethylammonium nitrate / dichloromethane / 20.5 h / -5 - 20 °C

3.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / Inert atmosphere; Reflux

4.1: hydrogenchloride; water / acetone / 2 h / Reflux

5.1: toluene / 15 h / 85 °C

5.2: 2 h

5.3: 1 h / Reflux

6.1: lithium hydroxide monohydrate / water; tetrahydrofuran; methanol / 5 h / Reflux

7.1: trichlorophosphate / chlorobenzene / 100 °C

8.1: bis(pinacol)diborane; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere

8.2: 90 °C / Inert atmosphere

With hydrogenchloride; dmap; 1,1'-bis-(diphenylphosphino)ferrocene; lithium hydroxide monohydrate; water; potassium acetate; tetramethylammonium nitrate; triethylamine; trifluoroacetic anhydride; bis(pinacol)diborane; trichlorophosphate; bis-triphenylphosphine-palladium(II) chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; chlorobenzene; acetone; toluene;

Reference yield:

5-nitro-pyridin-2-ylamine (4214-76-0,67476-67-9) → 9-(1-benzyl-3,6-dihydro-2H-pyridin-5-yl)-3H-pyrrolo[3,2-f][1,7]naphthyridine (1401447-95-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: sulfuric acid; potassium metaperiodate / 100 °C

1.2: 2.5 h / Heating

1.3: 20 °C

2.1: triethylamine / copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran; 2-ethylbutanamide / 2 h / Inert atmosphere

3.1: copper(l) iodide / N,N-dimethyl-formamide / 2 h / Inert atmosphere

4.1: sodium hydroxide / water; acetone / 0 °C

5.1: hydrogen / palladium 10% on activated carbon / dichloromethane; methanol / 20 °C

6.1: 120 - 130 °C

7.1: Dowtherm A / 250 °C

8.1: sodium hydroxide; water / ethanol / Reflux

9.1: Dowtherm A / 250 °C

10.1: trichlorophosphate / chlorobenzene / 100 °C

11.1: bis(pinacol)diborane; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere

11.2: 90 °C / Inert atmosphere

With 1,1'-bis-(diphenylphosphino)ferrocene; potassium metaperiodate; Dowtherm A; sulfuric acid; water; hydrogen; potassium acetate; triethylamine; bis(pinacol)diborane; sodium hydroxide; trichlorophosphate; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium 10% on activated carbon; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; 2-ethylbutanamide; water; N,N-dimethyl-formamide; chlorobenzene; acetone;

Reference yield:

1-benzyl-3-piperidone (40114-49-6) → 9-(1-benzyl-3,6-dihydro-2H-pyridin-5-yl)-3H-pyrrolo[3,2-f][1,7]naphthyridine (1401447-95-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran / 1 h / -78 °C

1.2: -78 - 20 °C

2.1: bis(pinacol)diborane; 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere

2.2: 90 °C / Inert atmosphere

With 1,1'-bis-(diphenylphosphino)ferrocene; n-butyllithium; potassium acetate; N-ethyl-N,N-diisopropylamine; bis(pinacol)diborane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,4-dioxane;

upstream raw materials:

1-benzyl-3-piperidone

4-chloro-7-azaindole

5-nitro-pyridin-2-ylamine

5-nitro-1H-pyrrolo[2,3-b]pyridine

Refernces