Acetic Acid → N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-3-hydroxy-N-methyl-5-trifluoromethyl-benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-N-[4-(2-chloro-phenyl)-pyridin-3-yl]-N-methyl-5-trifluoromethyl-benzamide (332 mg, 707 μmol, example 74) in dry THF (5 ml) was added triisopropyl borate (257 mg, 317 μl, 1.36 mmol, CAS RN 5419-55-6). n-BuLi (552 μl, 884 μmol, 1.6 M solution in n-hexane) was added dropwise at −78° C. The reaction mixture was stirred at −78° C. for 1.5 hours. A solution of AcOH (180 mg, 172 μl, 3.0 mmol) in water (0.2 ml) and hydrogen peroxide (103 mg, 92.8 μl, 1.06 mmol) was added at 0° C. The reaction mixture was stirred at room temperature for 18 hours and then poured on 30 ml 10% aqueous NaHCO3 solution and 30 ml EtOAc. The layers were separated and the aqueous layer was extracted a second time with 30 ml EtOAc. The combined organic layers were washed with 30 ml brine, dried over MgSO4, filtered and concentrated under vacuum. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Light yellow solid (77 mg, 27%). MS (ESI): m/z=407.077 [M+H]+.

Provenance & Evidence