5-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

Base Information

• Chemical Name: 5-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde
• CAS No.: 1190321-17-5
• Molecular Formula: C9H8N2O
• Molecular Weight: 160.17
• Hs Code.: 2933990090
• European Community (EC) Number: 802-246-1
• DSSTox Substance ID: DTXSID00596751
• Wikidata: Q82492084
• Mol file: 1190321-17-5.mol

Synonyms:5-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde;1190321-17-5;1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde, 5-methyl-;5-METHYL-7-AZAINDOLE-3-CARBALDEHYDE;SCHEMBL1713774;DTXSID00596751;AMY24610;MFCD12962781;AKOS006333537;SB14350;BS-19488;DB-061506;CS-0131073;A892698;5-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde, AldrichCPR

Chemical Property of 5-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

Chemical Property:

• PSA: 45.75000
• Density: 1.301 g/cm³
• LogP: 1.68380
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 160.063662883
• Heavy Atom Count: 12
• Complexity: 183

Purity/Quality:

97% ^*data from raw suppliers

5-Methyl-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(NC=C2C=O)N=C1

Technology Process of 5-Methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

There total 4 articles about 5-Methyl-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: 49.0%

hexamethylenetetramine (100-97-0) + 5-methyl-1H-pyrrolo[2,3-b]pyridine (824-52-2) → 5-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (1190321-17-5)

Guidance literature:

With water; acetic acid; for 4h; Reflux;

Reference yield:

(5-methyl-pyridin-2-yl)amine (1603-41-4) → 5-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (1190321-17-5)

Guidance literature:

Multi-step reaction with 4 steps

1: bromine / dichloromethane / 0.5 h / 20 °C / Cooling with ice

2: copper(l) iodide; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride / 80 °C / Inert atmosphere

3: sodium hydride / 1-methyl-pyrrolidin-2-one; mineral oil / 0.17 h / 100 °C / Cooling with ice

4: acetic acid; water / 4 h / Reflux

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; water; bromine; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; dichloromethane; mineral oil; 2: |Sonogashira Cross-Coupling;

Reference yield:

3-bromo-5-methylpyridin-2-amine (17282-00-7) → 5-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (1190321-17-5)

Guidance literature:

Multi-step reaction with 3 steps

1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride / 80 °C / Inert atmosphere

2: sodium hydride / 1-methyl-pyrrolidin-2-one; mineral oil / 0.17 h / 100 °C / Cooling with ice

3: acetic acid; water / 4 h / Reflux

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; water; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; mineral oil; 1: |Sonogashira Cross-Coupling;

upstream raw materials:

hexamethylenetetramine

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

(5-methyl-pyridin-2-yl)amine

3-bromo-5-methylpyridin-2-amine

Downstream raw materials:

(E)-5-methyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde oxime