4-Methoxybenzylamine → 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-(3-iodo-1-tosyl-1H-indol-5-yl)-5-(methylsulfinyl)-1,3,4-thiadiazole (423 mg, 0.757 mmol) in dioxane (3.0 mL) was added 4-methoxybenzylamine (0.294 mL, 2.268 mmol) at RT. The reaction was heated at 100° C. for 24 h. The solvent was removed and the residue was sonicated in MeOH and filtered. The filtrate was concentrated and the residue was purified with flash chromatography (eluting with 0-50% EtOAc in DCM) to give 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-thiadiazol-2-amine (245 mg, 0.397 mmol, 47%). MS (ESI, pos. ion) m/z: 617 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 8.40 (t, J=5.67 Hz, 1H), 8.16 (s, 1H), 8.03 (d, J=8.61 Hz, 1H), 7.94 (d, J=8.41 Hz, 2H), 7.79 (dd, J=8.71, 1.66 Hz, 1H), 7.62 (d, J=1.56 Hz, 1H), 7.42 (d, J=8.41 Hz, 2H), 7.32 (d, J=8.61 Hz, 2H), 6.92 (d, J=8.61 Hz, 2H), 4.46 (d, J=5.67 Hz, 2H), 3.73 (s, 3H), 2.33 (s, 3H).

Provenance & Evidence