Nitrogen → HCID 86711497, compound

Participants

Reaction Conditions

Reaction Steps

To a vial under N2 containing 5-(5-(3-bromobenzyl)-4-methyloxazol-2-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (27 mg, 0.056 mmol), tris(dibenzylideneacetone)dipalladium (10 mg, 0.011 mmol), Xphos (11 mg, 0.022 mmol), and Cs2CO3 (37 mg, 0.11 mmol) was added dioxane (1 mL, degassed with N2) followed by 1-methylpiperazine (10 μL, 0.084 mmol). The vial was sealed and heated to 120° C. in a Biotage microwave reactor for 60 min. The mixture was cooled to room temperature, filtered (Celite), and concentrated under reduced pressure. The crude oil was purified by HPLC to provide an orange oil: (7.8 mg, 28%): 1H NMR (600 MHz, DMSO-d6) δ ppm 8.20 (d, J=8.8 Hz, 2H), 7.61 (d, J=8.4 Hz, 2H), 7.23 (t, J=8.0 Hz, 1H), 6.95 (s, 1H), 6.91 (app. dd, J=8.3 Hz, 2.4 Hz, 1H), 6.77 (d, J=7.5 Hz, 1H), 4.17 (s, 2H), 3.84 (d, J=13.6 Hz, 1H), 3.51 (d, J=12.0 Hz, 1H), 3.19-1.09 (m, 2H), 2.94 (t, J=12.6 Hz, 2H), 2.85 (s, 3H), 2.61 (app. t, J=1.9 Hz, 1H), 2.38 (app. t, J=1.9 Hz, 1H), 2.27 (s, 3H); MS (ES+) C25H24F3N5O3 requires: 499, found: 500 [M+H]+.

Provenance & Evidence