Sodium Hydroxide → 5-(3-(6-(4-fluorophenyl)-pyrazin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

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Reaction Steps

A solution of 5-(3-(6-(4-fluorophenyl)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (200 mg, 0.309 mmol) in TFA (1 ml) was heated to 100° C. in microwave for 30 min. The mixture was cooled to RT and TFA was removed in vacuo to give the crude material (130 mg, 80%). MS (ESI, pos. ion) m/z: 527 (M+1). To a solution of crude 5-(3-(6-(4-fluorophenyl)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (130 mg, 0.247 mmol) in p-dioxane (1.3 mL) was added aq 10% NaOH (0.65 mL). The mixture was heated at 100° C. for 2 h and quenched with ice cold H2O. The resulting precipitate was filtered and washed with H2O. The crude was recrystallized with 10% MeOH/CHCl3 to give 5-(3-(6-(4-fluorophenyl)-pyrazin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (25 mg, 27.3%) as an off-yellow solid. MS (ESI, pos. ion) m/z: 374.0 (M+1); 1H-NMR (400 MHz, DMSO-d6): δ 12.11 (s, 1H), 9.17 (s, 1H), 9.06 (s, 1H), 9.00 (s, 1H), 8.53 (m, 1H), 8.37-8.34 (m, 2H), 8.75-8.73 (m, 1H), 7.64 (d, J=8 Hz, 1H), 7.49 (m, 2H), 7.12 (s, 2H).

Provenance & Evidence