Water → HCID 89808151, compound

Participants

Reaction Steps

Isopropyl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate (2.86 g, 7.8 mmol), 5-fluoro-2-methoxyphenyl boronic acid (2.64 g, 15.5 mmol), potassium carbonate (3.22 g, 23.3 mmol), Pd(OAc)2 (35 mg, 0.155 mmol), and x-Phos (146 mg, 0.31 mmol) were taken up in 15 mL dioxane and 7 mL water under nitrogen and stirred at 80° C. for 2 hours. Reaction then cooled to room temperature, filtered through celited plug with ethyl acetate. Reduced in vacuo and run through an isco silica column with hexane:ethyl acetate 75-100%. Product plus desbromo co-elute, reduced in Vacuo. Product recrystallized 2 times from ethyl acetate:Hexane, washed with heptanes dried to get 12 g product. 1H NMR (400 MHz, DMSO-d6) δ 8.73 (d, J=7.78 Hz, 1H), 8.50 (s, 1H), 8.29 (dd, J=3.14, 11.17 Hz, 1H), 7.04 (dd, J=5.02, 9.03 Hz, 1H), 6.95 (dd, J=3.26, 7.78 Hz, 1H), 6.79 (d, J=8.03 Hz, 1H), 4.77-4.85 (m, 1H), 3.87 (s, 3H), 3.70-3.78 (m, 4H), 3.48-3.56 (m, 4H), 1.21 (d, J=6.27 Hz, 6H). LRMS (ESI) m/z 414 [(M+H)]+, calc'd for C21H24N5O3: 413.4.

Provenance & Evidence