1H-Pyrrolo[3,2-b]pyridine-3-carboxylic acid, ethyl ester

Base Information

• Chemical Name: 1H-Pyrrolo[3,2-b]pyridine-3-carboxylic acid, ethyl ester
• CAS No.: 178896-76-9
• Molecular Formula: C₁₀H₁₀N₂O₂
• Molecular Weight: 190.202
• Mol file: 178896-76-9.mol

Synonyms:1H-Pyrrolo[3,2-b]pyridine-3-carboxylic acid, ethyl ester;Ethyl 1H-pyrrolo[3,2-b]pyridine-3-carboxylate;Ethyl 4-azaindole-3-carboxylate

Chemical Property of 1H-Pyrrolo[3,2-b]pyridine-3-carboxylic acid, ethyl ester

Chemical Property:

• PSA: 54.98000
• LogP: 1.73960

Purity/Quality:

97% ^*data from raw suppliers

Ethyl1H-pyrrolo[3,2-b]pyridine-3-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Pyrrolo[3,2-b]pyridine-3-carboxylic acid, ethyl ester

There total 4 articles about 1H-Pyrrolo[3,2-b]pyridine-3-carboxylic acid, ethyl ester 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:

2-Chloro-3-nitropyridine (5470-18-8,34515-82-7) → ethyl pyrrolo[3,2-b]pyridine-3-carboxylate (178896-76-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / Inert atmosphere

1.2: 4 h / 20 - 80 °C / Inert atmosphere

2.1: lithium chloride / dimethyl sulfoxide; water / 16 h / 80 °C / Inert atmosphere

3.1: N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere

4.1: acetic acid; iron / 2 h / 60 °C / Inert atmosphere

With iron; sodium hydride; acetic acid; lithium chloride; In N,N-dimethyl acetamide; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm401382v

Reference yield:

diethyl 2-(3-nitropyridin-2-yl)malonate (64362-41-0) → ethyl pyrrolo[3,2-b]pyridine-3-carboxylate (178896-76-9)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium chloride / dimethyl sulfoxide; water / 16 h / 80 °C / Inert atmosphere

2: N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere

3: acetic acid; iron / 2 h / 60 °C / Inert atmosphere

With iron; acetic acid; lithium chloride; In N,N-dimethyl acetamide; water; dimethyl sulfoxide;

DOI:10.1021/jm401382v

Reference yield:

ethyl 2-(3-nitro-pyridin-2-yl)-acetate (154078-83-8) → ethyl pyrrolo[3,2-b]pyridine-3-carboxylate (178896-76-9)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-dimethyl acetamide / 16 h / 80 °C / Inert atmosphere

2: acetic acid; iron / 2 h / 60 °C / Inert atmosphere

With iron; acetic acid; In N,N-dimethyl acetamide;

DOI:10.1021/jm401382v

upstream raw materials:

2-Chloro-3-nitropyridine

diethyl 2-(3-nitropyridin-2-yl)malonate

ethyl 2-(3-nitro-pyridin-2-yl)-acetate

ethyl 3-(dimethylamino)-2-(3-nitropyrid-2-yl)propenoate

Refernces

• 1、 Shirude, Pravin S.,Shandil, Radha,Sadler, Claire,Naik, Maruti,Hosagrahara, Vinayak,Hameed, Shahul,Shinde, Vikas,Bathula, Chandramohan,Humnabadkar, Vaishali,Kumar, Naveen,Reddy, Jitendar,Panduga, Vijender,Sharma, Sreevalli,Ambady, Anisha,Hegde, Naina,Whiteaker, James,McLaughlin, Robert E.,Gardner, Humphrey,Madhavapeddi, Prashanti,Ramachandran, Vasanthi,Kaur, Parvinder,Narayan, Ashwini,Guptha, Supreeth,Awasthy, Disha,Narayan, Chandan,Mahadevaswamy, Jyothi,Vishwas,Ahuja, Vijaykamal,Srivastava, Abhishek,Prabhakar, Kr,Bharath, Sowmya,Kale, Ramesh,Ramaiah, Manjunatha,Choudhury, Nilanjana Roy,Sambandamurthy, Vasan K.,Solapure, Suresh,Iyer, Pravin S.,Narayanan, Shridhar,Chatterji, Monalisa. "Azaindoles: Noncovalent DprE1 inhibitors from scaffold morphing efforts, kill Mycobacterium tuberculosis and are efficacious in vivo". . p. 9701 - 9708. Retrieved 2014/01/06.