Sodium Acetate → HCID 59222993, compound

Participants

Reaction Steps

To a suspension of 20% Pd(OH)2 (500 mg) and sodium acetate (368 mg, 4.5 mmol) and absolute EtOH (100 mL) under N2 in a 230 mL Corning shaker bottle was added {2-[4-(3,5-dichloro-2-trifluoromethylpyridin-4-yloxy)-phenyl]-ethyl}-(5,8-difluoroquinazolin-4-yl)-amine (1.15 g, 2.2 mmol). After deaerating, the bottle was charged with H2 (57 psig initial pressure) and shaken at room temp on Parr apparatus. After 24 h, another aliquot of 20% Pd(OH)2 was added, and the bottle was recharged with H2. After another 24 h, the reaction mixture was degassed, placed under nitrogen gas, and then filtered through Celite. The filtrate was evaporated and the residue was purified via preparative reverse phase LC (70% CH3CN/H2O, 0.5% H3PO4 eluant) to provide 390 mg of (5,8-difluoroquinazolin-4-yl)-{2-[4-(2-trifluoromethylpyridin-4-yloxy)-phenyl]-ethyl}-amine as an off-white powder, M.P. 95-96°. 1H NMR (400 MHz, CDCl3) δ 8.69 (s, 1H), 8.56 (d, J=5.7 Hz, 1H), 7.40-7.31 (m, 3H), 7.19 (d, J=2.4 Hz, 1H), 7.10-7.05 (m, 2H), 7.04-6.95 (m, 2H), 6.73 (dt, J=16.6, 5.4 Hz, 1H), 3.97 (q, J=6.9 Hz, 2H), 3.09 (t, J=7.1 Hz, 1H); MS: m/z 446.

Provenance & Evidence