Tert-butyl 4-(2-bromo-4-fluorophenyl)-4-(((4'-cyano-5-(trifluoromethyl)biphenyl-3-yl)methoxy)methyl)piperidine-1-carboxylate → 3'-(((4-(2-Bromo-4-fluorophenyl)piperidin-4-yl)methoxy)methyl)-5'-(trifluoromethyl)biphenyl-4-carbonitrile

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A solution of tert-butyl 4-(2-bromo-4-fluorophenyl)-4-(((4′-cyano-5-(trifluoromethyl)biphenyl-3-yl)methoxy)methyl)piperidine-1-carboxylate (50 mg, 0.077 mmol) in dichloromethane (0.5 mL) and trifluoroacetic acid (2 mL) was stirred at ambient temperature for 3 hours. The reaction was evaporated to dryness and the resulting residue was purified by chromatography on silica with gradient of methanol/dichloromethane of 2% to 10%. The product 3′-(((4-(2-bromo-4-fluorophenyl)piperidin-4-yl)methoxy)methyl)-5′-(trifluoromethyl)biphenyl-4-carbonitrile (29 mg, 69% yield) was obtained as a clear oil. 1H-NMR (CDCl3, 400 MHz) δ 7.74 (d, J=6.8 Hz, 2H), 7.68 (s, 1H), 7.58 (d, J=6.7 Hz, 2H), 7.36 (s, 1H), 7.33 (s, 1H), 7.22-7.33 (m, 2H), 7.03 (m, 1H), 4.49 (s, 2H), 3.88 (s, 2H), 3.25 (m, 2H), 2.94 (m, 2H), 2.85 (m, 2H), 2.23 (m, 2H). Mass spec.: 547.12 (M+H), HPLC (method 5) 3.37 min.

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