6-(4-benzyloxy-2-fluoro-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Base Information

• Chemical Name: 6-(4-benzyloxy-2-fluoro-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid
• CAS No.: 1431978-04-9
• Molecular Formula: C₂₅H₂₂FN₃O₄
• Molecular Weight: 447.466
• Mol file: 1431978-04-9.mol

Synonyms:6-(4-benzyloxy-2-fluoro-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Chemical Property of 6-(4-benzyloxy-2-fluoro-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(4-benzyloxy-2-fluoro-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

There total 4 articles about 6-(4-benzyloxy-2-fluoro-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid 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: 23.0%

2-Fluoro-4-benzyloxyphenylboronic acid (166744-78-1) + 6-chloro-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1431978-03-8) → 6-(4-benzyloxy-2-fluoro-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1431978-04-9)

Guidance literature:

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate; In 1,2-dimethoxyethane; water; at 80 ℃; for 0.25h; Inert atmosphere; Microwave irradiation;

Reference yield:

6-chloro-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester (1426918-16-2) → 6-(4-benzyloxy-2-fluoro-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1431978-04-9)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / tetrahydrofuran / 20 °C

2: sodium hydroxide; water / isopropyl alcohol / 2 h / 20 °C

3: potassium carbonate; bis(tri-t-butylphosphine)palladium⁽⁰⁾ / water; 1,2-dimethoxyethane / 0.25 h / 80 °C / Inert atmosphere; Microwave irradiation

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; water; potassium carbonate; toluene-4-sulfonic acid; sodium hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; water; isopropyl alcohol; 3: |Suzuki Coupling;

Reference yield:

6-chloro-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester (1431978-02-7) → 6-(4-benzyloxy-2-fluoro-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (1431978-04-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide; water / isopropyl alcohol / 2 h / 20 °C

2: potassium carbonate; bis(tri-t-butylphosphine)palladium⁽⁰⁾ / water; 1,2-dimethoxyethane / 0.25 h / 80 °C / Inert atmosphere; Microwave irradiation

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; water; potassium carbonate; sodium hydroxide; In 1,2-dimethoxyethane; water; isopropyl alcohol; 2: |Suzuki Coupling;

upstream raw materials:

6-chloro-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester

6-chloro-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester

2-Fluoro-4-benzyloxyphenylboronic acid

6-chloro-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Downstream raw materials:

4-[6-(2-fluoro-4-hydroxy-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-2-isopropyl-5,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

[6-(2-Fluoro-4-hydroxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-(5-isopropyl-2,2-dimethyl-piperazin-1-yl)-methanone

4-[6-(4-benzyloxy-2-fluoro-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-2-isopropyl-5,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester