1-[(tetrahydro-2H-pyran-4-yl)methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Base Information

• Chemical Name: 1-[(tetrahydro-2H-pyran-4-yl)methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
• CAS No.: 1220635-60-8
• Molecular Formula: C₁₅H₂₅BN₂O₃
• Molecular Weight: 292.186
• Mol file: 1220635-60-8.mol

Synonyms:1-[(tetrahydro-2H-pyran-4-yl)methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Chemical Property of 1-[(tetrahydro-2H-pyran-4-yl)methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Chemical Property:

• PSA: 45.51000
• LogP: 1.60890

Purity/Quality:

99%, ^*data from raw suppliers

1-((Tetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole ^*data from reagent suppliers

Safty Information:

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MSDS Files:

Useful:

Technology Process of 1-[(tetrahydro-2H-pyran-4-yl)methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

There total 2 articles about 1-[(tetrahydro-2H-pyran-4-yl)methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 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: 60.0%

→ 1-((tetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1220635-60-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 60 ℃; for 8h; Inert atmosphere;

Reference yield: 3.8%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + 4-(iodomethyl)tetrahydro-2H-pyran (101691-94-5) → 1-((tetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1220635-60-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 5h;

Reference yield:

6-bromo-3-chloro-isoquinoline (552331-06-3) + 1-((tetrahydro-2H-pyran-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1220635-60-8) → N-(4-(1,2-dimethyl-1H-imidazol-5-yl)-2-methoxyphenyl)-6-(1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-pyrazol-4-yl)isoquinolin-3-amine (1578482-64-0)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / 1,2-dimethoxyethane / 1 h / 140 °C / Microwave irradiation

2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene; N,N-dimethyl-formamide / 2 h / 160 °C / Microwave irradiation

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,2-dimethoxyethane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

pyrazole-4-boronic acid pinacol ester

4-(iodomethyl)tetrahydro-2H-pyran

Downstream raw materials:

N-(4-(1,2-dimethyl-1H-imidazol-5-yl)-2-methoxyphenyl)-6-(1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-pyrazol-4-yl)isoquinolin-3-amine

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