Application background and overview of quinoline-8-boronic acid sodium perborate tetrahydrate
Quinoline-8-boronic acid is a heterocyclic organic compound that can be used as a pharmaceutical synthesis intermediate in pure pyridine.
Application and preparation of quinoline-8-boronic acid
Quinoline-8-boronic acid is prepared as follows: 8-bromoquinoline (2.08g, 10mmol) is dissolved in 30ml of THF, and then n-butyllithium ( 4 mL, 2.5 M in hexanes). One hour after the addition, trimethyl borate (1.23 ml, 11 mmol) was added thereto at the same temperature. The resulting solution was stirred for 5 hours, then, 100 ml of 2MHCl was added thereto, and an extraction process was performed three times by using 60 ml of ethyl acetate. The obtained extracted fractions were combined, then dehydrated by using anhydrous magnesium sulfate, and distilled under reduced pressure. The obtained compound was separated and purified by silica gel column chromatography to yield 1.30 g (yield: 75%) of quinoline-8-boronic acid as a white solid. The obtained compound was confirmed by LC-MS.
Applications of quinoline-8-boronic acid
Quinoline-8-boronic acid can be used as a pharmaceutical synthesis intermediate. If the following reaction occurs:
The specific steps are as follows: add 1.73g (10.0mmol) quinoline-8-boronic acid, 2.02g (10.0mmol) 1-bromo-2-nitrobenzene, 0.58g (0.5mmol) Pd (PPh3) 3. Dissolve 0.16g (0.5mmol) tetrabutylammonium bromide (TBAB) and 3.18g (30.0mmol) Na2CO3 in 60mL of toluene/ethanol/H2O (3/3/1) mixed solution, then, The resulting mixture was stirred at a temperature of 80°C for 16 hours. The resulting reaction solution was cooled to room temperature, and then an extraction process was performed three times by using 60 mL of water and 60 mL of diethyl ether. The organic layer obtained therefrom was dried using magnesium sulfate, and the residue obtained by evaporating the solvent therefrom was separated-purified by silica gel column chromatography to obtain 2.13 g (yield: 85%) of compound 1-2. The compounds obtained were identified by LC-MS. C15H10N2O2: M+250.1
