6-(4-benzyloxy-2-fluorophenyl)-3-methyl-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester

Base Information

• Chemical Name: 6-(4-benzyloxy-2-fluorophenyl)-3-methyl-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester
• CAS No.: 1429171-73-2
• Molecular Formula: C₂₈H₂₈FN₃O₄
• Molecular Weight: 489.546
• Mol file: 1429171-73-2.mol

Synonyms:6-(4-benzyloxy-2-fluorophenyl)-3-methyl-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester

Chemical Property of 6-(4-benzyloxy-2-fluorophenyl)-3-methyl-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(4-benzyloxy-2-fluorophenyl)-3-methyl-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester

There total 4 articles about 6-(4-benzyloxy-2-fluorophenyl)-3-methyl-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester 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: 82.0%

2-Fluoro-4-benzyloxyphenylboronic acid (166744-78-1) + 6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester (1429171-71-0) → 6-(4-benzyloxy-2-fluorophenyl)-3-methyl-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester (1429171-73-2)

Guidance literature:

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate; In 1,2-dimethoxyethane; water; at 85 ℃; for 1.5h; Inert atmosphere;

Reference yield:

6-hydroxy-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester (1018166-61-4) → 6-(4-benzyloxy-2-fluorophenyl)-3-methyl-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester (1429171-73-2)

Guidance literature:

Multi-step reaction with 3 steps

1: phosphorus(V) oxybromide / toluene / 5 h / 110 °C

2: toluene-4-sulfonic acid / tetrahydrofuran / 96 h / 20 °C

3: bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate / 1,2-dimethoxyethane; water / 1.5 h / 85 °C / Inert atmosphere

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate; toluene-4-sulfonic acid; phosphorus(V) oxybromide; In tetrahydrofuran; 1,2-dimethoxyethane; water; toluene;

Reference yield:

6-bromo-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester (1396779-99-9) → 6-(4-benzyloxy-2-fluorophenyl)-3-methyl-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester (1429171-73-2)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / tetrahydrofuran / 96 h / 20 °C

2: bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate / 1,2-dimethoxyethane; water / 1.5 h / 85 °C / Inert atmosphere

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; 1,2-dimethoxyethane; water;

upstream raw materials:

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

2-Fluoro-4-benzyloxyphenylboronic acid

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

sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate

Downstream raw materials:

6-(4-benzyloxy-2-fluorophenyl)-3-methyl-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

{1-[6-(4-benzyloxy-2-fluorophenyl)-3-methyl-1-(tetrahydropyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-4-phenylpiperidin-4-yl}carbamic acid tert-butyl ester