Sodium Iodide → 5-(5-Methyl-1-{[3-(oxetan-3-yloxy)phenyl]methyl}-1H-1,2,4-triazol-3-yl)-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

Participants

Reaction Conditions

Reaction Steps

A mixture of K2CO3 (19.8 mg, 0.144 mmol), 3-((5-methyl-3-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-1H-1,2,4-triazol-1-yl)methyl)phenol (Example 59; 30.0 mg, 0.072 mmol), sodium iodide (21.6 mg, 0.144 mmol) and 3-bromooxetane (22 uL, 0.288 mmol) in DMF (0.36 mL) was stirred at 50° C. for 48 h. The crude mixture was diluted with H2O and extracted with 4:1 CHCl3:i-PrOH. The organic layer was dried over MgSO4, concentrated under reduced pressure, and the residue was purified using Prep-HPLC to furnish the title compound; MS (ES+) C22H18F3N5O4 requires: 473. found 474 [M+H]+; 1H-NMR (600 MHz, CD3OD) δ ppm 8.28 (d, J=8.8 Hz, 2H), 7.35 (d, J=8.2 Hz, 2H), 7.28 (m, 1H), 6.86 (d, J=7.8 Hz, 1H), 6.64 (m, 2H), 5.42 (s, 2H), 5.18 (m, 1H), 4.95 (m, 2H), 4.74 (m, 2H), 2.54 (s, 3H).

Provenance & Evidence