Diisopropylethylamine → HCID 90011193, compound

Participants

Reaction Steps

Step-3: 1′-(5-Bromopyridin-2-yl)-4,4-dimethyl-5′-(trifluoromethyl)-1H, 1′H-[3,3′-bipyrazol]-5(4H)-one: To a stirred and (0° C.) cooled solution of step-2 intermediate (2.0 g, 4.76 mmol) and DIPEA (1.66 mL, 9.52 mmol) in DCM (20 mL) was added a solution of triphosgene (560 mg, 1.90 mmol) in DCM (5 mL) over a period of 10 min. The reaction mixture was warmed to room temperature and then stirred overnight. Reaction was cooled down to 0° C. and then quenched with ice water (5 mL). Water (25 mL) was added to the reaction followed by DCM (50 mL). The layers were separated and the aqueous layer was extracted with DCM (2×50 mL). The combined organic layers were washed with brine (50 mL), dried (Na2SO4) and filtered. The filtrate was rotary evaporated to afford 1.50 g (78%) of the title compound as semisolid. 1HNMR (400 MHz, CDCl3) δ 8.85 (s, 1H, D2O exchangeable), 8.59 (d, J=2.0 Hz, 1H), 8.02 (dd, J=2.0 & 8.0 Hz, 1H), 7.78 (d, J=8.0 Hz, 1H), 7.31 (s, 1H), 1.60 (s, 6H); ESI-MS (m/z) 402, 404 [(MH)+, Br79,81].

Provenance & Evidence