Chemical Properties
white crystalline powder
Uses
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine is an organoborane compound used in the preparation of of polyazatriaryl ligands by sequential borylation/Suzuki-Miyaura coupling. 3-Pyridineboronic Acid Pinacol E ster is used in the preparation of pyrrolo[2,3-b]pyridine derivatives as kinase modulators.
Uses
3-Pyridineboronic Acid Pinacol Ester is an organoborane compound used in the preparation of polyazatriaryl ligands by sequential borylation/Suzuki-Miyaura coupling. 3-Pyridineboronic Acid Pinacol Ester is used in the preparation of pyrrolo[2,3-b]pyridine derivatives as kinase modulators.
Synthesis
In a nitrogen-protected glove box, a benzene solution of silica-3p-TPP ([P] content 0.11 mmol/g, 45.5 mg, 0.005 mmol P, 1 mol% P), anhydrous degassed benzene (0.8 mL), and [PdCl(η3-cinnamyl)]2 (0.65 mg, 0.00125 mmol, 0.5 mol% Pd) (0.2 mL) was added sequentially to an oven-dried 10 mL glass tube pre-fitted with a magnetic stirrer. After stirring for 5 min, KOAc (147 mg, 1.5 mmol), bis(pinacolato)diboron (2,140 mg, 0.55 mmol) and 3-chloropyridine (63.3 mg, 0.50 mmol) were added sequentially. The reaction tube was sealed with a screw cap and then removed from the glove box, and the reaction was stirred at 25°C for 10 hours. After completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad (eluting with Et2O) and the filtrate was concentrated under reduced pressure. To the residue was added the internal standard 1,1,2,2-tetrachloroethane, and the yield of the product 3-pyridineboronic acid pinacol ester was 95% as determined by 1H NMR. The crude product was purified by silica gel column chromatography to afford the target compound 3-pyridineboronic acid pinacol ester (87.0 mg, 0.40 mmol, 80% yield).
References
[1] ChemCatChem, 2014, vol. 6, # 5, p. 1340 - 1348
[2] RSC Advances, 2018, vol. 8, # 25, p. 13643 - 13648
[3] Angewandte Chemie - International Edition, 2007, vol. 46, # 28, p. 5359 - 5363
[4] Chemistry Letters, 2014, vol. 43, # 5, p. 584 - 586
[5] Patent: WO2010/110782, 2010, A1. Location in patent: Page/Page column 46-47
