Triethylamine → HCID 90010990, compound

Participants

Reaction Conditions

Reaction Steps

Step-1: 1-(5-Bromopyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-3-carbaldehyde: To a stirred solution of 1-(5-bromopyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-3-carboxylic acid (6.20 g, 18.45 mmol), in DMF (50 mL) was successively added EDC.HCl (4.24 g, 22.14 mmol), HOBT (3.11 g, 20.29 mmol), N,O-dimethylhydroxylamine hydrochloride (2.70 g, 27.7 mmol) and triethylamine (5.14 mL, 36.9 mmol). After stirring the reaction mixture at 65° C. for 12 h, the reaction was cooled to RT. Water (60 mL) was added to the above reaction followed by ethyl acetate (100 mL). The layers were separated and aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), dried (Na2SO4) and filtered. 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 4.20 g (60%) of the 1-(5-bromopyridin-2-yl)-N-methoxy-N-methyl-5-(trifluoromethyl)-1H-pyrazole-3-carboxamide as white solid. 1HNMR (400 MHz, DMSO-d6) δ 8.74 (d, J=2.5 Hz, 1H), 8.37 (dd, J=2.5 & 8.5 Hz, 1H), 7.88 (d, J=8.5 Hz, 1H), 7.50 (s, 1H), 3.77 (s, 3H), 3.34 (s, 3H); ESI-MS (m/z) 379, 381 [(MH)+, Br79,81].

Provenance & Evidence