Sodium Hydroxide → 5-(3-(4-(2-fluorophenyl)pyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

Participants

Reaction Steps

To a solution of 5-(3-(4-(2-fluorophenyl)pyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (250 mg, 0.38 mmol) in TFA (1.25 mL) was heated to 100° C. in a microwave for 30 min. The mixture was cooled to RT and TFA was removed in vacuo to give the crude material after washing with Et2O. MS (ESI, pos. ion) m/z: 527 (M+1). To a solution of crude 5-(3-(4-(2-fluorophenyl)pyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (250 mg, 0.47 mmol) in p-dioxane (2.5 mL) was added aq. 10% NaOH (1.25 mL) and the reaction was heated at 100° C. for 2 h. The reaction was quenched with ice cold H2O and the resulting precipitate was filtered, washed with ice cold H2O and dried. The crude product was recrystallized with 10% MeOH/CHCl3 to give 5-(3-(4-(2-fluorophenyl)pyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (40 mg, 23%) as an off yellow solid. MS (ESI, pos. ion) m/z: 373.1 (M+1); 1H-NMR (400 MHz, DMSO-d6): δ 12.13 (s, 1H), 9.08 (s, 1H), 8.92 (m, 1H) 8.47 (d, J=2.8 Hz, 1H) 8.33-8.30 (m, 1H), 7.72-7.76 (m, 6H), 7.51-7.53 (m, 3H).

Provenance & Evidence