5-(3-(6-morpholinopyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine → 5-(3-(6-morpholinopyridin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

Participants

Reaction Steps

The solution of 5-(3-(6-morpholinopyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (0.07 g, 0.135 mmol) in 10% KOH (0.7 mL) and THF (0.7 mL) was heated at 100° C. for 5 h. Then the reaction mass was evaporated to dryness and ice cold H2O (5 mL) was added and extracted with EtOAc. The combined organic layers were washed with brine, dried, filtered and concentrated. The crude product was recrystallized with 10% MeOH in CHCl3 to give 5-(3-(6-morpholinopyridin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (0.02 g, 40.8%) as a pale yellow solid. MS (ESI, pos. ion) m/z: 363 (M+1); 1H NMR (DMSO-d6, 400 MHz): δ 11.74 (s, 1H), 8.91 (s, 1H), 8.11 (s, 1H), 7.64-7.52 (m, 3H), 7.19 (d, J=7.6 Hz, 1H), 7.04 (s, 2H), 6.65 (d, J=8.4 Hz, 1H), 3.79 (s, 4H), 3.58 (s, 4H).

Provenance & Evidence