5-(6-chloropyridin-2-yl)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine

Base Information

• Chemical Name: 5-(6-chloropyridin-2-yl)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine
• CAS No.: 1401732-47-5
• Molecular Formula: C₂₀H₁₇ClN₄O
• Molecular Weight: 364.834
• Mol file: 1401732-47-5.mol

Synonyms:5-(6-chloropyridin-2-yl)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine

Chemical Property of 5-(6-chloropyridin-2-yl)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(6-chloropyridin-2-yl)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine

There total 4 articles about 5-(6-chloropyridin-2-yl)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine 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:

5-bromo-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine (1111638-42-6) + 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (652148-92-0) → 5-(6-chloropyridin-2-yl)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine (1401732-47-5)

Guidance literature:

With caesium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; at 100 ℃; for 12h; Inert atmosphere; Sealed tube;

Reference yield:

3-methyl-5-nitropyrazolo<3,4-b>pyridine (62908-83-2) → 5-(6-chloropyridin-2-yl)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine (1401732-47-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: palladium on activated charcoal / ethanol / 5 h / 20 °C

2.1: hydrogen bromide; sodium nitrite / copper(I) bromide / water / 4 h / -5 - 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / -5 - 20 °C

3.2: 0 - 20 °C / Reflux

4.1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane / 12 h / 100 °C / Inert atmosphere; Sealed tube

With hydrogen bromide; sodium hydride; caesium carbonate; sodium nitrite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium on activated charcoal; copper(I) bromide; In 1,2-dimethoxyethane; ethanol; water; N,N-dimethyl-formamide; mineral oil;

Reference yield:

3-methyl-1H-pyrazolo[3,4-b]pyridin-5-amine (1186608-73-0) → 5-(6-chloropyridin-2-yl)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine (1401732-47-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogen bromide; sodium nitrite / copper(I) bromide / water / 4 h / -5 - 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / -5 - 20 °C

2.2: 0 - 20 °C / Reflux

3.1: caesium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,2-dimethoxyethane / 12 h / 100 °C / Inert atmosphere; Sealed tube

With hydrogen bromide; sodium hydride; caesium carbonate; sodium nitrite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(I) bromide; In 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; mineral oil;

upstream raw materials:

3-methyl-5-nitropyrazolo<3,4-b>pyridine

3-methyl-1H-pyrazolo[3,4-b]pyridin-5-amine

5-bromo-3-methyl-1H-pyrazolo[3,4-b]pyridine

5-bromo-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine

Refernces