Pyrazole → HCID 24969552, compound

Participants

Reaction Conditions

Reaction Steps

(4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-({6-chloro-3-[4-fluoro-2-methoxy-5-(propan-2-yl)phenyl]pyridin-2-yl}methyl)-4-methyl-1,3-oxazolidin-2-one chloride (40 mg, 0.066 mmol) and pyrazole (5.40 mg, 0.079 mmol) were dissolved in dioxane (0.7 mL) in a 2-5 mL microwave vial. Cesium carbonate (43.1 mg, 0.132 mmol) and copper(I) iodide (12.6 mg, 0.066 mmol) were added and the mixture was degassed. N,N-dimethylethylenediamine (23.3 mg, 0.264 mmol) was added before sealing the system and heating (thermally) to 110° C. overnight. The reaction was cooled and filtered over Celite® (ethyl acetate wash) and the filtrate was concentrated and was purified by reverse phase HPLC to yield (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-({6-chloro-3-[4-fluoro-2-methoxy-5-(propan-2-yl)phenyl]pyridin-2-yl}methyl)-4-methyl-1,3-oxazolidin-2-one (5.5 mg, 8.64 μmol). 1H NMR (CD3OD, 500 MHz) δ 8.63 (s, 1H), 7.99 (s, 1H), 7.93 (m, 3H), 7.79 (s, 1H), 7.75 (d, J=8.2 Hz, 1H), 7.17 (br s, 1H), 6.88 (d, J=12.3 Hz, 1H), 6.57 (s, 1H), 5.84 (m, 1H), 4.85 (m, 1H), 4.21 (m, 2H), 3.81 (s, 3H), 3.21 (m, 1H), 1.29 (m, 6H), 0.64 (d, J=41.1 Hz, 3H). SPA=55.8 nM

Provenance & Evidence