N-(3-methoxybenzyl)-6-(1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

Base Information

• Chemical Name: N-(3-methoxybenzyl)-6-(1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide
• CAS No.: 1296200-83-3
• Molecular Formula: C₁₉H₁₇N₅O₂
• Molecular Weight: 347.376
• Mol file: 1296200-83-3.mol

Synonyms:

Chemical Property of N-(3-methoxybenzyl)-6-(1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(3-methoxybenzyl)-6-(1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

There total 5 articles about N-(3-methoxybenzyl)-6-(1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide 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-4-amino-5-iodopyridine (800402-12-4) → N-(3-methoxybenzyl)-6-(1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide (1296200-83-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate / N,N-dimethyl-formamide / 110 °C

2: triethylamine; HATU / N,N-dimethyl-formamide

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / ethanol; toluene / 145 °C

With 1,4-diaza-bicyclo[2.2.2]octane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium diacetate; potassium carbonate; triethylamine; HATU; In ethanol; N,N-dimethyl-formamide; toluene; 3: Suzuki coupling;

DOI:10.1016/j.bmcl.2011.09.083

Reference yield:

4-Amino-2-chloropyridine (14432-12-3) → N-(3-methoxybenzyl)-6-(1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide (1296200-83-3)

Guidance literature:

Multi-step reaction with 4 steps

1: silver(II) sulfate; iodine / ethanol / 72 h / 20 °C

2: 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate / N,N-dimethyl-formamide / 110 °C

3: triethylamine; HATU / N,N-dimethyl-formamide

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / ethanol; toluene / 145 °C

With 1,4-diaza-bicyclo[2.2.2]octane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; silver(II) sulfate; iodine; palladium diacetate; potassium carbonate; triethylamine; HATU; In ethanol; N,N-dimethyl-formamide; toluene; 4: Suzuki coupling;

DOI:10.1016/j.bmcl.2011.09.083

Reference yield:

6-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid (800401-54-1) + 3-METHOXYBENZYLAMINE (5071-96-5) → N-(3-methoxybenzyl)-6-(1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide (1296200-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; HATU / N,N-dimethyl-formamide

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / ethanol; toluene / 145 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; triethylamine; HATU; In ethanol; N,N-dimethyl-formamide; toluene; 2: Suzuki coupling;

DOI:10.1016/j.bmcl.2011.09.083

upstream raw materials:

2-chloro-4-amino-5-iodopyridine

4-Amino-2-chloropyridine

6-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid

3-METHOXYBENZYLAMINE