Chemical Properties
White to light yellow crystal powder
Uses
2-Pyridineboronic Acid is used in organic synthesis as a reagent in Suzuki cross-coupling reactions, for example in the synthesis of aryl- and heteroaryl-substituted 3-benzyloxyisothiazoles and novel fluorescent 3-aryl- and 3-methyl-7-aryl-[1,2,3]triazolo[1,5-a]pyridines.
Synthesis
The general procedure for the synthesis of 2-pyridineboronic acid from 2-bromopyridine and triisopropyl borate was as follows: 1.58 g (10 mmol) of 2-bromopyridine and 3.76 g (20 mmol) of triisopropyl borate were dissolved in a solvent mixture of 14 mL of anhydrous toluene and 7 mL of THF, stirred and cooled at -30 °C. Under nitrogen protection, 6.25 mL (10 mmol) of 1.6 M n-butyllithium hexane solution was added slowly dropwise with a syringe. After the dropwise addition, the reaction mixture was continued to be stirred at -30 °C for 3 h. Subsequently, it was brought to room temperature and stirred for another 3 h. The completion of the reaction was monitored by TLC. 1 mL of concentrated hydrochloric acid was slowly added to the reaction mixture and stirred for 1 hr at room temperature before the mixture was poured into 200 mL of ice water. The pH was adjusted to 8 with saturated sodium bicarbonate solution, stirred, and extracted three times with 50 mL of dichloromethane. The organic phases were combined, washed with 100 mL of 5% brine and dried over anhydrous sodium sulfate. The desiccant was removed by filtration, the filtrate was concentrated to dryness by rotary evaporator, and the residue was purified by silica gel column chromatography to give 1.00 g of 2-pyridineboronic acid in 81% yield.
References
[1] Patent: CN107903250, 2018, A. Location in patent: Paragraph 0025; 0029; 0030; 0031
[2] Patent: CN108047215, 2018, A. Location in patent: Paragraph 0032; 0036-0038
[3] Patent: CN108047214, 2018, A. Location in patent: Paragraph 0024; 0025; 0029; 0031
[4] Patent: KR2015/121394, 2015, A. Location in patent: Paragraph 0154-0157
