(4-Chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanol → HCID 118006161, compound

Participants

Reaction Steps

n-BuLi (2.5 M in THF, 0.60 mL, 1.5 mmol) was added dropwise over a 3 minute period to a mixture of 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (0.5 g, 1.16 mmol, Intermediate 12: step d) and 1-(4-(1-methyl-1H-1,2,3-triazole-5-carbonyl)piperidin-1-yl)ethanone (0.27 g, 1.16 mmol, Intermediate 52: step b) in dry THF (8 mL) at −78° C. Stirring was continued at −78° C. for 10 minutes. The reaction mixture was then immersed in an ice bath and stirred at 0° C. for 1 hour. The reaction was then quenched with saturated aqueous NaHCO3, diluted with water and extracted with EtOAc (2×). The EtOAc extracts were dried over Na2SO4, filtered, evaporated in vacuo and purified by FCC (0-10% MeOH in DCM, gradient) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.10 (s, 2H), 7.80 (d, J=8.6 Hz, 1H), 7.64 (d, J=8.1 Hz, 2H), 7.45 (d, J=8.1 Hz, 2H), 6.25 (s, 1H), 4.41-4.57 (m, 0.5H), 4.34 (s, 2.5H), 4.01 (s, 3H), 3.67-3.94 (m, 0.5H), 3.63 (d, J=3.5 Hz, 3H), 3.08-3.23 (m, 0.5H), 2.82-2.96 (m, 0.5H), 2.56-2.74 (m, 1.5H), 2.27-2.44 (m, 0.5H), 1.84-2.05 (m, 4H), 1.65-1.84 (m, 0.5H), 0.76-1.38 (m, 3H); MS (ESI) 588.

Provenance & Evidence