ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Base Information

• Chemical Name: ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate
• CAS No.: 942920-55-0
• Molecular Formula: C10H9 Br N2 O2
• Molecular Weight: 269.098
• Hs Code.: 2933990090
• Mol file: 942920-55-0.mol

Synonyms:ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate;

Chemical Property of ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Chemical Property:

• PKA: 10.96±0.40(Predicted)
• PSA: 54.98000
• Density: 1.624g/cm3
• LogP: 2.50210
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

There total 5 articles about ethyl 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate 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: 100.0%

ethyl 1H-pyrrolo[2,3-b]pyridine-2-carboxylate-7-oxide (287384-82-1) → 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester (942920-55-0)

Guidance literature:

With tetrabutylammomium bromide; Methanesulfonic anhydride; In 1,2-dimethoxyethane; at 0 - 20 ℃; regioselective reaction;

DOI:10.1021/jm901870q

Reference yield: 91.0%

ethyl 1-(benzenesulfonyl)-4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate → 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester (942920-55-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 65 ℃; for 2h;

Reference yield:

1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester (221675-35-0) → 4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester (942920-55-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 25 °C

2: tetramethylammonium bromide; Methanesulfonic anhydride / chloroform / 16 h / 0 - 25 °C

With tetramethylammonium bromide; 3-chloro-benzenecarboperoxoic acid; Methanesulfonic anhydride; In dichloromethane; chloroform;

upstream raw materials:

ethyl 1H-pyrrolo[2,3-b]pyridine-2-carboxylate-7-oxide

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

1-(benzenesulfonyl)-4-bromo-1H-pyrrolo[2,3-b]pyridine

4-bromo-7-azaindole

Downstream raw materials:

4-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid

4-[1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]-pyridine-2-carboxylic acid

ethyl 4-[(4-nitrophenyl)amino]-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

ethyl 4-(4,4,5,5-tetramethyl-1,3,2-diozaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Refernces

• 1、 -. "DIHYDROISOQUINOLINE-2(1H)-CARBOXAMIDE AND RELATED COMPOUNDS AND THEIR USE IN TREATING MEDICAL CONDITIONS". . . Retrieved 2019/11/04.
• 2、 -. "Pyrrolo [2,3,B] Pyridine Derivatives Useful As RAF Kinase Inhibitors". Page/Page column 18-19. . Retrieved 2009/01/24.