4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Base Information

• Chemical Name: 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile
• CAS No.: 920965-87-3
• Molecular Formula: C8H4ClN3
• Molecular Weight: 177.593
• Hs Code.: 2933990090
• Mol file: 920965-87-3.mol

Synonyms:4-chloro-3-cyano-1H-pyrrolo[2,3-b]pyridine;1H-Pyrrolo[2,3-b]pyridine-3-carbonitrile,4-chloro;4-CHLORO-3-CYANO-7-AZAINDOLE;

Chemical Property of 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Chemical Property:

• PKA: 10.58±0.40(Predicted)
• PSA: 52.47000
• Density: 1.5g/cm3
• LogP: 2.08798
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

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

4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

There total 8 articles about 4-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile 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: 70.0%

(E)-4-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde oxime (1004991-98-3) → 4-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (920965-87-3)

Guidance literature:

(E)-4-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde oxime; With thionyl chloride; In dichloromethane; at 25 ℃; for 4h; Heating / reflux;

With sodium hydrogencarbonate; In water;

Reference yield:

4-chloro-7-azaindole (55052-28-3) → 4-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (920965-87-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: aluminum (III) chloride / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

1.2: 48 h / 20 °C / Inert atmosphere

2.1: ammonia / 1,4-dioxane / 8 h / 130 °C / Microwave irradiation; Inert atmosphere

3.1: hexamethylenetetramine; acetic acid / water / 18 h / 100 °C / Inert atmosphere

4.1: hydroxylamine hydrochloride; sodium hydroxide / ethanol / 21 h / 20 - 50 °C / Inert atmosphere

5.1: thionyl chloride / dichloromethane / 20 °C / Inert atmosphere

With aluminum (III) chloride; thionyl chloride; hexamethylenetetramine; hydroxylamine hydrochloride; ammonia; acetic acid; sodium hydroxide; In 1,4-dioxane; ethanol; dichloromethane; water;

Reference yield:

7-oxy-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile; methanesulphonic acid salt → 4-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (920965-87-3)

Guidance literature:

With methanesulfonyl chloride; In N,N-dimethyl-formamide; at 80 ℃; for 2h; Heating / reflux;

upstream raw materials:

(E)-4-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde oxime

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

4-chloro-7-azaindole

4-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

Downstream raw materials:

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

4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine

4-chloro-3-iodo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine

Refernces

• 1、 -. "AMINE DERIVATIVES USEFUL AS ANTICANCER AGENTS". Page/Page column 91. . Retrieved 2010/11/30.
• 2、 -. "NOVEL COMPOUNDS". Page/Page column 36. . Retrieved 2008/06/13.