Cesium carbonate → HCID 86711904, compound

Participants

Reaction Conditions

Reaction Steps

5-(1-(3-Bromobenzyl)-5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (40 mg, 0.0833 mmol), Cs2CO3 (54 mg, 0.167 mmol), XPhos (16 mg, 0.0333 mmol), Pd2(dba)3 (15 mg, 0.0167 mmol), and N′,N′-dimethylethane-1,2-diamine were placed in a microwave reaction vessel and dioxane (1 mL), which had been degassed by bubbling N2 through it for 10 min, was added. The reaction was heated by microwave irradiation at 120° C. for 1 h. Purification by prep-HPLC (MeCN/H2O 30%-70% MeCN containing 0.1% TFA) afforded N,N-dimethyl-2-((3-((5-methyl-3-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-1H-1,2,4-triazol-1-yl)methyl)phenyl)amino)ethanaminium trifluoroacetate as a thin film (1.5 mg, 4%). MS (ES+) C23H24F3N7O2 requires: 487. found 488 [M+H]+; 1H NMR (600 MHz, CDCl3) δ 8.32-8.24 (m, 2H), 7.34 (d, J=8.1 Hz, 2H), 7.20-7.15 (m, 1H), 6.63-6.56 (m, 2H), 6.54-6.51 (m, 1H), 5.35 (s, 2H), 3.53 (t, J=5.4 Hz, 2H), 3.28 (t, J=5.4 Hz, 2H), 2.87 (s, 6H), 2.54 (s, 3H).

Provenance & Evidence