Trifluoroacetic acid → (4-Chloro-3-phenyl-2-(trifluoromethyl)quinolin-6-yl)(piperidin-4-yl)(pyridin-3-yl)methanol

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Reaction Steps

A solution of tert-butyl 4-((4-chloro-3-phenyl-2-(trifluoromethyl)quinolin-6-yl)(hydroxy)(pyridin-3-yl)methyl)piperidine-1-carboxylate (313 mg, 0.520 mmol, Example 69) in DCM (6 mL) was treated with 1.8 mL of TFA, stirred for 3 hours, and concentrated. The residue was partitioned between saturated NaHCO3 aqueous solution and DCM. The organic layer was dried (Na2SO4), filtered and concentrated to dryness to provide the title compound as a light brown solid. 1H NMR (400 MHz, CDCl3) δ 8.86 (s, 1H), 8.55 (s, 1H), 8.44 (d, J=4.55 Hz, 1H), 8.21 (d, J=9.09 Hz, 1H), 7.89-7.96 (m, 2H), 7.46-7.53 (m, 4H), 7.23-7.32 (m, 2H), 3.23-3.36 (m, 2H), 2.77-2.91 (m, 3H), 1.66-1.86 (m, 4H).

Provenance & Evidence