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

Base Information

• Chemical Name: 4-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde
• CAS No.: 1000340-35-1
• Molecular Formula: C8H5BrN2O
• Molecular Weight: 225.0421
• Hs Code.: 2933990090
• Mol file: 1000340-35-1.mol

Synonyms:1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 4-bromo-;

Chemical Property of 4-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

Chemical Property:

• Boiling Point: 416.668 °C at 760 mmHg
• PKA: 11.45±0.40(Predicted)
• Flash Point: 205.794 °C
• PSA: 45.75000
• Density: 1.83 g/cm³
• LogP: 2.13790
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

There total 2 articles about 4-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde 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: 86.0%

hexamethylenetetramine (100-97-0) + 4-bromo-7-azaindole (348640-06-2) → 4-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (1000340-35-1)

Guidance literature:

With acetic acid; In water; at 100 ℃; for 16h;

Reference yield: 79.0%

1-(4-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-N,N-dimethylmethanamine (1198277-82-5) + hexamethylenetetramine (100-97-0) → 4-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (1000340-35-1)

Guidance literature:

With propionic acid; at 120 ℃; Reflux;

Reference yield:

4-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (1000340-35-1) → 4-(8-((4-(4-fluorophenyl)-1-isopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)methyl)-2-oxo-1-oxa-3,8-diazaspiro[4.5]decan-3-yl)benzoic acid

Guidance literature:

Multi-step reaction with 3 steps

1.1: caesium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C

1.2: 2 h / 80 °C

2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate / water; 1,4-dioxane / 0.5 h / 120 °C / Microwave irradiation; Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine; acetic acid; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 20 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium tris(acetoxy)borohydride; potassium carbonate; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1021/acsmedchemlett.8b00306

upstream raw materials:

1-(4-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-N,N-dimethylmethanamine

hexamethylenetetramine

4-bromo-7-azaindole

Downstream raw materials:

4-(4-fluorophenyl)-1-isopropyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

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

Refernces

• 1、 -. "3-SUBSTITUTED-1H-INDOLE, 3-SUBSTITUTED-1H-PYRROLO[2,3-B]PYRIDINE AND 3-SUBSTITUTED-1H-PYRROLO[3,2-B]PYRIDINE COMPOUNDS, THEIR USE AS MTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESES". Page/Page column 120. . Retrieved 2010/04/06.