1H-Pyrrolo[2,3-b]pyridine, 2-(4-chlorophenyl)-

Base Information

• Chemical Name: 1H-Pyrrolo[2,3-b]pyridine, 2-(4-chlorophenyl)-
• CAS No.: 139962-69-9
• Molecular Formula: C₁₃H₉ClN₂
• Molecular Weight: 228.681
• Mol file: 139962-69-9.mol

Synonyms:

Chemical Property of 1H-Pyrrolo[2,3-b]pyridine, 2-(4-chlorophenyl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1H-Pyrrolo[2,3-b]pyridine, 2-(4-chlorophenyl)-

There total 7 articles about 1H-Pyrrolo[2,3-b]pyridine, 2-(4-chlorophenyl)- 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:

methyl 2-[bis(tert-butoxycarbonyl)amino]nicotinate (877593-10-7) → 2-(4-Chloroyphenyl)<1H>-pyrrolo<2,3-b>pyridine (139962-69-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / 0 - 23 °C / Inert atmosphere

1.2: -10 - 20 °C / Inert atmosphere

2.1: pyridine; thionyl chloride / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: 3-(2,6-diethylphenyl)-4,5-dimethylthiazol-3-ium perchlorate; caesium carbonate / 1,4-dioxane / 36 h / 23 °C / Inert atmosphere; Glovebox

4.1: methanesulfonic acid / 40 °C / Inert atmosphere

With pyridine; lithium aluminium tetrahydride; thionyl chloride; methanesulfonic acid; 3-(2,6-diethylphenyl)-4,5-dimethylthiazol-3-ium perchlorate; caesium carbonate; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1039/c6cc04735a

Reference yield:

methyl 2-aminonicotinate (14667-47-1) → 2-(4-Chloroyphenyl)<1H>-pyrrolo<2,3-b>pyridine (139962-69-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dmap / dichloromethane / 48 h / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.5 h / 0 - 23 °C / Inert atmosphere

2.2: -10 - 20 °C / Inert atmosphere

3.1: pyridine; thionyl chloride / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: 3-(2,6-diethylphenyl)-4,5-dimethylthiazol-3-ium perchlorate; caesium carbonate / 1,4-dioxane / 36 h / 23 °C / Inert atmosphere; Glovebox

5.1: methanesulfonic acid / 40 °C / Inert atmosphere

With pyridine; dmap; lithium aluminium tetrahydride; thionyl chloride; methanesulfonic acid; 3-(2,6-diethylphenyl)-4,5-dimethylthiazol-3-ium perchlorate; caesium carbonate; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1039/c6cc04735a

Reference yield:

2-(tert-butoxycarbonyl)amino-3-chloromethylpyridine → 2-(4-Chloroyphenyl)<1H>-pyrrolo<2,3-b>pyridine (139962-69-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 3-(2,6-diethylphenyl)-4,5-dimethylthiazol-3-ium perchlorate; caesium carbonate / 1,4-dioxane / 36 h / 23 °C / Inert atmosphere; Glovebox

2: methanesulfonic acid / 40 °C / Inert atmosphere

With methanesulfonic acid; 3-(2,6-diethylphenyl)-4,5-dimethylthiazol-3-ium perchlorate; caesium carbonate; In 1,4-dioxane;

DOI:10.1039/c6cc04735a

upstream raw materials:

4-Cyanochlorobenzene

3-Methylpyridine

methyl 2-[bis(tert-butoxycarbonyl)amino]nicotinate

methyl 2-aminonicotinate