Sodium Chloride → 3-[6-Methyl-4-(4-trifluoromethyl-phenyl)pyridin-2-yl]-benzeneboronic acid

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Reaction Steps

To a solution of 2-(3-bromo-phenyl)-6-methyl-4-(4-trifluoromethyl-phenyl)-pyridine (example E.21) (4.00 g, 10.2 mmol) and triisopropyl borate (2.23 g, 11.8 mmol) in THF (60 mL) at −78° C. was added n-BuLi (1.6 M in hexane, 6.50 mL, 10.4 mmol) keeping the internal temperature below −65° C. Stirring was continued at −78° C. for 45 min, again triisopropyl borate (1.11 g, 5.9 mmol) and n-BuLi (1.6 M in hexane, 3.25 mL, 5.2 mmol) were added and stirring was continued at −78° C. for 30 min. A 1 M aqueous solution of NaH2PO4.2H2O was added, saturated with solid NaCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and the solvent was removed in vacuum to give the title compound as a yellow solid (4.39 g, 96%). MS (ISP) 358.2 [(M+H)+]; mp 140° C. (dec.).

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