2,6-Dimethylpyridine-4-boronic acid, pinacol ester

Synthesis

General procedure for the synthesis of 2,6-dimethylpyridine-4-boronic acid pinacol ester from 4-bromo-2,6-dimethylpyridine and bis(boronic acid) pinacol ester: to 4-bromo-2,6-dimethylpyridine (1.00 g, 5.38 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) ( 1.64 g, 6.45 mmol), PdCl2(dppf) (393 mg, 0.537 mmol), and KOAc (1.58 g, 16.12 mmol) was added to a mixture of degassed dioxane solution (2 mL). The reaction mixture was heated and stirred at 85 °C for 18 hours. Upon completion of the reaction, the mixture was dissolved in EtOAc and filtered through a Celite pad. The filtrate was concentrated in vacuum to afford the crude product 2,6-dimethylpyridine-4-boronic acid pinacol ester (1.88 g, 8.07 mmol, quantitative yield) as a brown solid.

References

[1] Patent: WO2016/196644, 2016, A1. Location in patent: Paragraph 274; 275
[2] Patent: WO2018/102452, 2018, A2. Location in patent: Paragraph 258; 259