2-Morpholinopyridine-4-boronic acid, pinacol ester

Base Information

• Chemical Name: 2-Morpholinopyridine-4-boronic acid, pinacol ester
• CAS No.: 888721-86-6
• Molecular Formula: C15H23BN2O3
• Molecular Weight: 290.17
• Hs Code.: 2934999090
• Mol file: 888721-86-6.mol

Synonyms:4-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]morpholine;

Chemical Property of 2-Morpholinopyridine-4-boronic acid, pinacol ester

Chemical Property:

• Vapor Pressure: 2.71E-08mmHg at 25°C
• Refractive Index: 1.53
• Boiling Point: 450.1 °C at 760 mmHg
• Flash Point: 226 °C
• PSA: 43.82000
• Density: 1.13 g/cm³
• LogP: 1.28240

Purity/Quality:

97% ^*data from raw suppliers

2-Morpholinopyridine-4-boronic acid, pinacol ester AldrichCPR ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Morpholinopyridine-4-boronic acid, pinacol ester

There total 2 articles about 2-Morpholinopyridine-4-boronic acid, pinacol 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: 56.0%

4-(4-bromopyridin-2-yl)morpholine (1040377-12-5) + bis(pinacol)diborane (73183-34-3) → 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine (888721-86-6)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In N,N-dimethyl-formamide; at 80 ℃; Inert atmosphere;

Reference yield:

4-bromo-2-fluoropyridine (128071-98-7) → 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine (888721-86-6)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / 66 h / 100 °C

2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 80 °C / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; triethylamine; In N,N-dimethyl-formamide; 2: |Suzuki Coupling;

Reference yield: 63.0%

4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine (888721-86-6) + N-({5-bromo-2-[(3-{[(tert-butyldimethylsilyl)oxy]methyl}pyridin-2-yl)sulfanyl]-3-chlorophenyl}methyl)-2-methylpropane-2-sulfinamide → N-({2-[(3-{[(tert-butyldimethylsilyl)oxy]methyl}pyridin-2-yl)sulfanyl]-3-chloro-5-[2-(morpholin-4-yl)pyridin-4-yl]phenyl}methyl)-2-methylpropane-2-sulfinamide

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; water; at 120 ℃; for 16h; Inert atmosphere;

upstream raw materials:

4-bromo-2-fluoropyridine

4-(4-bromopyridin-2-yl)morpholine

bis(pinacol)diborane

Downstream raw materials:

C₃₉H₃₆ClN₅O₃

C₄₀H₃₆N₆O₃

4-(4-(4-chloro-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)pyridine-2-yl)morpholine

(4-(4-ethoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)pyridin-2-yl)morpholine

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