Ethanol → HCID 118005945, compound

Participants

Reaction Steps

A 250 mL Parr flask containing (4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanol (155 mg, 0.32 mmol, Example 14a) was added EtOH (25 mL) and Et3N (1 mL) followed by 5% palladium on carbon (75 mg). The flask was pressurized to 50 psi with H2 gas and shaken for 18 hours. HPLC analysis indicated the conversion was approximately 40%. The reaction mixture was filtered through Celite® and concentrated. The residue was dissolved in MeOH and run in the H-cube hydrogenation apparatus using a 10% Pd/C cartridge at 50° C., 70 psi H2 and 1.2 ml/minute (all with closed loop recycling). After the cycling was complete, the solution was concentrated to dryness and the residue was chromatographed on silica gel (10% EtOAc-DCM increasing to 5% MeOH-DCM) to provide the title compound as a white solid. 1H NMR (500 MHz, CDCl3) δ ppm 7.76 (d, J=8.5 Hz, 1H), 7.58-7.47 (m, 3H), 7.40-7.31 (m, 3H), 7.30-7.20 (m, 2H), 6.94 (d, J=7.7 Hz, 1H), 4.05 (overlapping s, 6H), 2.51 (s, 3H), 2.45 (s, 3H). MS (ESI): mass calcd. for C26H23F3N2O2, 452.2, m/z found 453.2 [M+H]+.

Provenance & Evidence