Br[C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([F:19])[CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=1.[B:20](OC(C)C)([O:25]C(C)C)[O:21]C(C)C.[Li]CCCC.Cl>C1COCC1.C1(C)C=CC=CC=1>[F:19][C:17]1[CH:18]=[C:2]([B:20]([OH:25])[OH:21])[CH:3]=[C:4]([O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=2)[CH:16]=12-(3-Bromo-5-fluorophenoxy)-5-(trifluoromethyl)pyridine (2 g, 0.005 mol) and tri-isopropyl borate (1.6 mL, 0.007 mol) were dissolved in dry THF (40 mL) and toluene (10 mL) under inert atmosphere and cooled to −78° C. n-BuLi (4.48 mL, 0.005 mol) was then added dropwise at −78° C. The reaction was warmed to −20° C. and 2N HCl (2 mL) was added and then the mixture was warmed to RT. The reaction mixture was concentrated and extracted with ethyl acetate three times. The organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness to give the title compound (2.71 g, 70%); m/z (300.4, M− H−).
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