2-Methylquinoline-6-boronic acid pinacol ester

Base Information

• Chemical Name: 2-Methylquinoline-6-boronic acid pinacol ester
• CAS No.: 1022090-86-3
• Molecular Formula: C16H20BNO2
• Molecular Weight: 269.151
• Mol file: 1022090-86-3.mol

Synonyms:2-Methylquinoline-6-boronic acid pinacol ester;2-Methylquinoline-6-boronic acid pinacol ester 95%;2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

Chemical Property of 2-Methylquinoline-6-boronic acid pinacol ester

Chemical Property:

• Melting Point: 83-89°C
• PSA: 31.35000
• LogP: 2.84240
• Storage Temp.: ?20°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline is used as a reactant in the synthesis of 1H-pyrazol-3(2H)-ones as potent and selective inhibitors of protein kinase R-like endoplasmic reticulum kinase.

Technology Process of 2-Methylquinoline-6-boronic acid pinacol ester

There total 2 articles about 2-Methylquinoline-6-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: 29.0%

2-methylquinoline (91-63-4) + bis(pinacol)diborane (73183-34-3) → 2-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (939052-79-6) + 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-quinoline (1022090-86-3)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 5, 6-dimethyl-1,10-phenanthroline; In tetrahydrofuran; at 70 ℃; for 5h; regioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201801229

Reference yield:

6-Bromo-2-methyl-quinoline (877-42-9) + bis(pinacol)diborane (73183-34-3) → 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-quinoline (1022090-86-3)

Guidance literature:

With bis(triphenylylphosphine)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100 ℃; for 1h; Microwave irradiation;

Reference yield: 54.0%

2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-quinoline (1022090-86-3) + 4-(2-amino-3-iodo-4-methylbenzoyl)-1-methyl-2,5-diphenyl-1H-pyrazol-3(2H)-one → 4-(2-amino-4-methyl-3-(2-methylquinolin-6-yl)benzoyl)-1-methyl-2,5-diphenyl-1H-pyrazol-3(2H)-one hydrochloride

Guidance literature:

2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-quinoline; 4-(2-amino-3-iodo-4-methylbenzoyl)-1-methyl-2,5-diphenyl-1H-pyrazol-3(2H)-one; With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; water; toluene; at 100 ℃; for 8h; Sealed tube; Inert atmosphere;

With hydrogenchloride; In methanol; dichloromethane; water; toluene; for 0.75h; Sealed tube; Inert atmosphere;

DOI:10.1021/jm5017494

upstream raw materials:

6-Bromo-2-methyl-quinoline

bis(pinacol)diborane

2-methylquinoline

Downstream raw materials:

C₂₅H₁₇F₆N₃O

C₂₅H₁₅F₆N₃O₂

C₁₆H₁₄N₂