Sodium Hydroxide → HCID 90011400, compound

Participants

Reaction Conditions

Reaction Steps

Step-1: 5-Bromo-2-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridine: A mixture of 4,4,4-trifluoro-1-(furan-2-yl)butane-1,3-dione (7.0 g, 34.0 mmol) and 5-bromo-2-hydrazinylpyridine hydrochloride (7.62 g, 34.0 mmol) in acetic acid (20 mL) was stirred at 70° C. for 1.5 h. The reaction mixture was cooled to room temperature (RT) and then diluted with ethyl acetate (200 mL) and basified with aqueous sodium hydroxide solution (10%, pH 7-8). The resulting slurry was filtered and the filtrate was washed with water (50 mL), dried (Na2SO4) and filtered. The filtrate was rotary evaporated and the crude product was purified by flash column chromatography (silica gel, 20% ethyl acetate-hexanes as eluent) to afford 10 g (82%) of the title compound as white semisolid. 1HNMR (400 MHz, CDCl3) δ 8.54 (brs, 1H), 8.02 (dd, J=2.5 & 8.5 Hz, 1H), 7.64 (d, J=8.5 Hz, 1H), 7.45 (d, J=1.5 Hz, 1H), 6.93 (s, 1H), 6.62 (d, J=3.5 Hz, 1H), 6.47 (dd, J=3.5 & 1.5 Hz, 1H); ESI-MS (m/z) 358, 360 [(MH)+, Br79,81].

Provenance & Evidence