Cesium carbonate → HCID 72202359, compound

Participants

Reaction Conditions

Reaction Steps

Step-1: 2,6-Difluoro-N-(6-(3-formyl-5-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl) benzamide: In a sealed tube containing a dioxane (20 mL) and cesium carbonate (2.54 g, 7.81 mmol) was purged with nitrogen gas for 10 min and then 1-(5-bromopyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-3-carbaldehyde (prepared in step-1 of the intermediate-12; 1.0 g, 3.12 mmol), 2,6-difluorobenzamide (736 mg, 4.69 mmol) and xanthphos (180 mg, 0.31 mmol) were sequentially added. The resulting mixture was thoroughly deoxygenated by purging nitrogen gas for another 15 min and then palladium (II) acetate (35 mg, 0.15 mmol) was added to the above mixture. The sealed tube was capped and stirred at 130° C. for 6 h. The reaction mixture was then cooled to room temperature and filtered through celite. The filtrate was rotary evaporated and the crude product was purified by flash column chromatography (silica gel, ethyl acetate-hexanes system as eluent) to afford 700 mg (56%) of the title compound as white solid. 1HNMR (400 MHz, CDCl3) δ 10.09 (s, 1H), 8.63 (d, J=2.0 Hz, 1H), 8.60 (dd, J=2.0 & 8.0 Hz, 1H), 8.00 (brs, 1H, D2O Exchangeable), 7.93 (d, J=8.0 Hz, 1H), 7.59-7.53 (m, 1H), 7.36 (s, 1H), 7.09 (t, J=8.0 Hz, 2H); ESI-MS (m/z) 397 (MH)+

Provenance & Evidence