Dimethylformamide → HCID 90011519, compound

Participants

Reaction Steps

Step-1: 1-(5-Bromopyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-3-carboxamide: To a (0° C.) cooled solution of 1-(5-bromopyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-3-carboxylic acid (5.0 g, 14.88 mmol) in DCM (50 mL) was added oxalyl chloride (3.91 mL, 44.6 mmol) followed by catalytic amount of DMF (0.14 mL, 1.78 mmol). The resulting mixture was stirred at room temperature for 1 h. The excess of oxalyl chloride was removed under vacuum and the residue was again diluted with DCM (100 mL). Aqueous ammonium hydroxide solution (29.0 mL, 744 mmol) was added drop-wise to the above mixture at 0° C. and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated under vacuum and concentrate was diluted with ethyl acetate (100 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (100 mL), dried (Na2SO4) and filtered. The filtrate was rotary evaporated to afford 4.0 g (80%) of the title compound as white solid. 1HNMR (400 MHz, DMSO-d6) δ 8.73 (d, J=2.0 Hz, 1H), 8.41 (dd, J=2.0 & 8.0 Hz, 1H), 8.09 (s, 1H, D2O exchangeable), 7.97 (d, J=8.0 Hz, 1H), 7.70 (s, 1H, D2O exchangeable), 7.52 (s, 1H); ESI-MS (m/z) 335, 337 [(MH)+, Br79,81].

Provenance & Evidence